DD244552A5 - Verfahren zur herstellung von azetidin-derivaten - Google Patents

Verfahren zur herstellung von azetidin-derivaten Download PDF

Info

Publication number: DD244552A5
Authority: DD; German Democratic Republic
Prior art keywords: nickel; azetidine; formula; salt; water
Prior art date: 1985-04-16

Application number

DD86289076A

Other languages

German (de)

English (en)

Inventor

Pieter A Verbrugge

Waal Jannetje De

David W Sopher

Original Assignee

��@��@��@��@�K@�Kk��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-04-16

Filing date

1986-04-14

Publication date

1987-04-08

1986-04-14 Application filed by ��@��@��@��@�K@�Kk�� filed Critical ��@��@��@��@�K@�Kk��

1987-04-08 Publication of DD244552A5 publication Critical patent/DD244552A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 34
230000008569 process Effects 0.000 title claims abstract description 16
238000004519 manufacturing process Methods 0.000 title description 3
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical class C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 title description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 71
229910052759 nickel Inorganic materials 0.000 claims abstract description 42
230000003647 oxidation Effects 0.000 claims abstract description 20
238000007254 oxidation reaction Methods 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
GNVWVYIAQBJHGV-UHFFFAOYSA-N azetidin-3-ylmethanol Chemical class OCC1CNC1 GNVWVYIAQBJHGV-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
-1 N-substituted azetidine carboxylate Chemical class 0.000 abstract description 29
238000006114 decarboxylation reaction Methods 0.000 abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract description 6
229910052783 alkali metal Inorganic materials 0.000 abstract description 5
150000001340 alkali metals Chemical class 0.000 abstract description 5
229910052739 hydrogen Inorganic materials 0.000 abstract description 5
239000001257 hydrogen Substances 0.000 abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 3
150000001342 alkaline earth metals Chemical group 0.000 abstract description 3
239000003513 alkali Substances 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract description 2
238000010511 deprotection reaction Methods 0.000 abstract description 2
239000013067 intermediate product Substances 0.000 abstract description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
125000003944 tolyl group Chemical group 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000007787 solid Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000000047 product Substances 0.000 description 17
238000003756 stirring Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 16
CWDWGQLVRSTJCN-UHFFFAOYSA-N 1-benzylazetidine-3,3-dicarboxylic acid Chemical compound C1C(C(=O)O)(C(O)=O)CN1CC1=CC=CC=C1 CWDWGQLVRSTJCN-UHFFFAOYSA-N 0.000 description 13
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
AOFFCJVJVZRCBL-UHFFFAOYSA-N [1-benzyl-3-(hydroxymethyl)azetidin-3-yl]methanol Chemical compound C1C(CO)(CO)CN1CC1=CC=CC=C1 AOFFCJVJVZRCBL-UHFFFAOYSA-N 0.000 description 12
GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical class OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
238000005868 electrolysis reaction Methods 0.000 description 10
239000003792 electrolyte Substances 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
IFGBBXJGLBGHJN-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonylazetidine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(C(O)=O)C1 IFGBBXJGLBGHJN-UHFFFAOYSA-N 0.000 description 9
XVFKOLZJNKMHNL-UHFFFAOYSA-N 1-benzylazetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=CC=C1 XVFKOLZJNKMHNL-UHFFFAOYSA-N 0.000 description 9
238000006056 electrooxidation reaction Methods 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000000376 reactant Substances 0.000 description 8
230000004913 activation Effects 0.000 description 7
238000011065 in-situ storage Methods 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000004743 Polypropylene Substances 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
ZDTSHVGCSDAFJH-UHFFFAOYSA-N (1-benzylazetidin-3-yl)methanol Chemical compound C1C(CO)CN1CC1=CC=CC=C1 ZDTSHVGCSDAFJH-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 4
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 4
229910017604 nitric acid Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
MBIJMMNQEXUYCL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonylazetidine-3,3-dicarboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(C(O)=O)(C(O)=O)C1 MBIJMMNQEXUYCL-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
BFLVHFJMYNKSEK-UHFFFAOYSA-N 1-nitroazetidine-3-carboxylic acid Chemical compound OC(=O)C1CN([N+]([O-])=O)C1 BFLVHFJMYNKSEK-UHFFFAOYSA-N 0.000 description 2
LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000005708 Sodium hypochlorite Substances 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
IISOMQJAPNZTPN-UHFFFAOYSA-N [3-(hydroxymethyl)-1-(4-methylphenyl)sulfonylazetidin-3-yl]methanol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(CO)(CO)C1 IISOMQJAPNZTPN-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
MHYMJKUZMUYNOJ-UHFFFAOYSA-N azetidin-1-ylmethanol Chemical compound OCN1CCC1 MHYMJKUZMUYNOJ-UHFFFAOYSA-N 0.000 description 2
GETUVALQSXUKQD-UHFFFAOYSA-N azetidine-3,3-dicarboxylic acid Chemical class OC(=O)C1(C(O)=O)CNC1 GETUVALQSXUKQD-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
239000010959 steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004804 winding Methods 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VYCUOOZEPUQLNF-UHFFFAOYSA-N 1-(1-phenylethyl)azetidine-3,3-dicarboxylic acid Chemical compound C=1C=CC=CC=1C(C)N1CC(C(O)=O)(C(O)=O)C1 VYCUOOZEPUQLNF-UHFFFAOYSA-N 0.000 description 1
VKCBXONEZGIOSP-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonylazetidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC1 VKCBXONEZGIOSP-UHFFFAOYSA-N 0.000 description 1
XVIVTATXHQQFFW-UHFFFAOYSA-N 1-benzhydrylazetidine-3,3-dicarboxylic acid Chemical compound C1C(C(=O)O)(C(O)=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 XVIVTATXHQQFFW-UHFFFAOYSA-N 0.000 description 1
IXMOEAHDRKNAAG-UHFFFAOYSA-N 1-benzhydrylazetidine-3-carbonitrile Chemical compound C1C(C#N)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 IXMOEAHDRKNAAG-UHFFFAOYSA-N 0.000 description 1
UNEKSSHIQHZUFD-UHFFFAOYSA-N 1-benzyl-3-(hydroxymethyl)azetidine-3-carboxylic acid Chemical compound C1C(CO)(C(O)=O)CN1CC1=CC=CC=C1 UNEKSSHIQHZUFD-UHFFFAOYSA-N 0.000 description 1
SNKTZBNDUVWOAZ-UHFFFAOYSA-N 1-nitrosoazetidine Chemical compound O=NN1CCC1 SNKTZBNDUVWOAZ-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
RZWGTXHSYZGXKF-UHFFFAOYSA-N 2-(2-methylphenyl)acetic acid Chemical compound CC1=CC=CC=C1CC(O)=O RZWGTXHSYZGXKF-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010021929 Infertility male Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
208000007466 Male Infertility Diseases 0.000 description 1
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical class [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000220317 Rosa Species 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
JAXQPBINKGFTPK-UHFFFAOYSA-N [3-(hydroxymethyl)azetidin-3-yl]methanol Chemical compound OCC1(CO)CNC1 JAXQPBINKGFTPK-UHFFFAOYSA-N 0.000 description 1
XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical class [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
230000009471 action Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
VDFLYDCPHUPMAO-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1.OC(=O)C1CNC1 VDFLYDCPHUPMAO-UHFFFAOYSA-N 0.000 description 1
150000001539 azetidines Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
OCCIDTXLZAHUSF-UHFFFAOYSA-L disodium;1-benzylazetidine-3,3-dicarboxylate Chemical compound [Na+].[Na+].C1C(C(=O)[O-])(C([O-])=O)CN1CC1=CC=CC=C1 OCCIDTXLZAHUSF-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000003487 electrochemical reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86289076A 1985-04-16 1986-04-14 Verfahren zur herstellung von azetidin-derivaten DD244552A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858509746A GB8509746D0 (en)	1985-04-16	1985-04-16	Preparing azetidine derivatives

Publications (1)

Publication Number	Publication Date
DD244552A5 true DD244552A5 (de)	1987-04-08

Family

ID=10577742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86289076A DD244552A5 (de)	1985-04-16	1986-04-14	Verfahren zur herstellung von azetidin-derivaten

Country Status (21)

Country	Link
US (2)	US4778577A (da)
EP (1)	EP0199413A3 (da)
JP (1)	JPS61238991A (da)
KR (1)	KR860008134A (da)
CN (1)	CN86102422A (da)
AU (1)	AU584412B2 (da)
BR (1)	BR8601677A (da)
DD (1)	DD244552A5 (da)
DK (1)	DK169386A (da)
ES (1)	ES8707494A1 (da)
GB (1)	GB8509746D0 (da)
GR (1)	GR860978B (da)
HU (1)	HU201303B (da)
IL (1)	IL78491A (da)
NO (1)	NO861447L (da)
NZ (1)	NZ215815A (da)
OA (1)	OA08276A (da)
PH (1)	PH22393A (da)
SU (1)	SU1586512A3 (da)
TN (1)	TNSN86056A1 (da)
ZA (1)	ZA862766B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8524024D0 (en) *	1985-09-30	1985-11-06	Shell Int Research	Preparation of azetidine-3-carboxylic acid
DE69722538T2 (de) *	1996-09-06	2004-04-29	Sumitomo Chemical Co., Ltd.	Verfahren zur Herstellung von optisch aktiver Azetidin-2-Carbonsäure
ES2193524T3 (es) *	1997-04-24	2003-11-01	Kaneka Corp	Procedimiento de preparacion de acido azetidino-2-carboxilico.
DE10117222B4 (de)	2001-04-06	2004-12-30	Goldschmidt Ag	Verfahren zur Herstellung von Glycinderivaten
WO2002088298A1 (en) *	2001-04-27	2002-11-07	The Procter & Gamble Company	Compounds, compositions, and methods for controlling biofilms
CA2534550A1 (en) *	2003-09-15	2005-03-24	Novartis Ag	1, 3-disubstituted azetidine derivatives for use as ccr-3 receptor antagonists in the treatment of inflammatory and allergic diseases
JP5211318B2 (ja) *	2007-03-28	2013-06-12	国立大学法人長崎大学	α，α−ジ置換環状含窒素化合物の製造方法
MX2009011998A (es) *	2007-05-10	2009-11-19	Pfizer Ltd	Derivados de azetidina y su uso como antagonistas de prostaglandina e2.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1169027A (en) *	1966-11-19	1969-10-29	Beecham Group Ltd	Azetidine Derivatives
GB8300860D0 (en) *	1983-01-13	1983-02-16	Shell Int Research	Azetidine compounds
US4496440A (en) *	1984-06-04	1985-01-29	The Dow Chemical Company	Oxidation of hydrophobic --CH2 OH compounds at oxidized nickel anodes
GB8415614D0 (en) *	1984-06-19	1984-07-25	Shell Int Research	Azetidine derivatives
GB8415615D0 (en) *	1984-06-19	1984-07-25	Shell Int Research	Preparing azetidine derivatives
EP0168852B1 (en) *	1984-06-19	1989-07-26	Shell Internationale Researchmaatschappij B.V.	Azetidine derivatives and their preparation

1985
- 1985-04-16 GB GB858509746A patent/GB8509746D0/en active Pending
1986
- 1986-04-12 CN CN198686102422A patent/CN86102422A/zh active Pending
- 1986-04-14 NZ NZ215815A patent/NZ215815A/xx unknown
- 1986-04-14 AU AU56064/86A patent/AU584412B2/en not_active Ceased
- 1986-04-14 NO NO861447A patent/NO861447L/no unknown
- 1986-04-14 DK DK169386A patent/DK169386A/da not_active IP Right Cessation
- 1986-04-14 PH PH33647A patent/PH22393A/en unknown
- 1986-04-14 KR KR1019860002829A patent/KR860008134A/ko not_active Withdrawn
- 1986-04-14 BR BR8601677A patent/BR8601677A/pt unknown
- 1986-04-14 ES ES553949A patent/ES8707494A1/es not_active Expired
- 1986-04-14 HU HU861559A patent/HU201303B/hu not_active IP Right Cessation
- 1986-04-14 SU SU864027253A patent/SU1586512A3/ru active
- 1986-04-14 ZA ZA862766A patent/ZA862766B/xx unknown
- 1986-04-14 GR GR860978A patent/GR860978B/el unknown
- 1986-04-14 JP JP61084413A patent/JPS61238991A/ja active Pending
- 1986-04-14 OA OA58831A patent/OA08276A/xx unknown
- 1986-04-14 IL IL78491A patent/IL78491A/xx unknown
- 1986-04-14 DD DD86289076A patent/DD244552A5/de not_active IP Right Cessation
- 1986-04-15 EP EP86200639A patent/EP0199413A3/en not_active Withdrawn
- 1986-04-16 US US06/852,857 patent/US4778577A/en not_active Expired - Lifetime
- 1986-04-16 TN TNTNSN86056A patent/TNSN86056A1/fr unknown
1988
- 1988-06-09 US US07/204,479 patent/US4855452A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUT42755A (en)	1987-08-28
US4855452A (en)	1989-08-08
IL78491A0 (en)	1986-08-31
HU201303B (en)	1990-10-28
EP0199413A3 (en)	1987-05-06
TNSN86056A1 (fr)	1990-01-01
IL78491A (en)	1989-03-31
KR860008134A (ko)	1986-11-12
AU5606486A (en)	1986-10-23
US4778577A (en)	1988-10-18
JPS61238991A (ja)	1986-10-24
NO861447L (no)	1986-10-17
SU1586512A3 (ru)	1990-08-15
AU584412B2 (en)	1989-05-25
ZA862766B (en)	1986-11-26
CN86102422A (zh)	1987-01-28
GB8509746D0 (en)	1985-05-22
ES553949A0 (es)	1987-08-01
BR8601677A (pt)	1986-12-16
PH22393A (en)	1988-08-12
DK169386A (da)	1986-10-17
GR860978B (en)	1986-08-06
DK169386D0 (da)	1986-04-14
EP0199413A2 (en)	1986-10-29
NZ215815A (en)	1989-07-27
OA08276A (en)	1987-10-30
ES8707494A1 (es)	1987-08-01

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2439879A1 (de)	1976-03-04	Verfahren zur oxidation von olefinverbindungen
DE60100620T2 (de)	2004-03-11	Gezielte elektrochemische reduktion von halogenierten 4-amino-picolinsäuren
EP0574667A1 (de)	1993-12-22	Verfahren zur Herstellung von 2,2,6,6-Tetramethylpiperidin-N-oxyl und in seiner 4-Stellung substituierten Derivaten
DE19548428C1 (de)	1997-08-28	2-Alkylmerkapto-4-(trifluormethyl)-benzoesäureester sowie ein Verfahren zu ihrer Herstellung
DE3874195T2 (de)	1993-02-11	Reduktion von carbonsaeureestern.
US4778577A (en)	1988-10-18	Process for preparing azetidine derivatives; and intermediates therein
DE1593865A1 (de)	1971-02-25	Verfahren zur Isolierung von 4,4'-Diaminodiphenylmethan aus Polyphenylmethylenpolyamingemischen
EP0064154A1 (de)	1982-11-10	Verfahren zur Herstellung von blauen Eisenhexacyanoferrat-III-Pigmenten
DE3725481C2 (da)	1993-03-25
DE3443303A1 (de)	1986-06-05	Verfahren zur herstellung von 3-hydroxy-3-methylglutarsaeure
EP0533132B1 (de)	1994-11-02	Verfahren zur Oxidation von Hydroxymethylpyridinderivaten zu Pyridincarbonsäurederivaten
DE69127687T2 (de)	1998-01-15	Verfahren zur Herstellung von Nepinolon
CH624671A5 (en)	1981-08-14	Process for the preparation of 2-oxopyrrolidine-N-alkylamides
DE3152459C2 (da)	1987-09-17
DD249909A5 (de)	1987-09-23	Verfahren zur herstellung von carbocyclischen acetidin-3-saeuren und deren salzen
DE2331712A1 (de)	1975-01-23	Verfahren zur herstellung von 2methoxy-3,6-dichlorbenzoesaeure
DE2460156C2 (de)	1983-03-24	Verfahren zur Herstellung von Diaceton-2-ketogulonsäure
DE2363634C3 (de)	1978-01-12	Verfahren zur Herstellung von N-Phosphonmethylglycin
DE69604247T2 (de)	2000-03-30	2-Cyanopiperazin und ihre Verwendung für die Synthese von biologisch wirksamen Stoffen
DE3928290A1 (de)	1991-02-28	Verfahren zur herstellung von aminobenzylalkoholen
DE2331711A1 (de)	1975-01-23	Verfahren zur selektiven elektrolytischen entbromierung
DE2723121C2 (de)	1979-04-19	Verfahren zur Herstellung von Alkylthiosemicarbaziden
AT375343B (de)	1984-07-25	Verfahren zur herstellung der neuen 1-methyl-5(p-toluoyl)-3-carboxypyrrol-2-essigsaeure
DE1147950B (de)	1963-05-02	Verfahren zur Herstellung von Hexahydropyrimidin-4, 6-dion-Derivaten
DE2459233C2 (de)	1983-06-01	Verfahren zur Herstellung von Hydrochinon