CA1127159A - Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation - Google Patents

Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation

Info

Publication number: CA1127159A
Authority: CA; Canada
Prior art keywords: cis; azabicyclo; anhydride; reaction; trans
Prior art date: 1978-07-06
Legal status (The legal status 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 status listed.): Expired

Application number

CA381,217A

Other languages

English (en)

Inventor

Willy D. Kollmeyer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

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.)

1978-07-06

Filing date

1981-07-06

Publication date

1982-07-06

1978-07-06 Priority claimed from US05/922,407 external-priority patent/US4183857A/en

1981-07-06 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1981-07-06 Priority to CA381,217A priority Critical patent/CA1127159A/fr

1982-07-06 Application granted granted Critical

1982-07-06 Publication of CA1127159A publication Critical patent/CA1127159A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000005228 3‐azabicyclo[3.1.0]hexanes Chemical class 0.000 title description 2
JEISWFNRNZRSHM-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1C2CC2C(=O)N1CC1=CC=CC=C1 JEISWFNRNZRSHM-UHFFFAOYSA-N 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 18
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
150000008064 anhydrides Chemical class 0.000 claims description 11
RLWFMZKPPHHHCB-WSOKHJQSSA-N (1r,2s)-cyclopropane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@H]1C[C@H]1C(O)=O RLWFMZKPPHHHCB-WSOKHJQSSA-N 0.000 claims description 6
238000004821 distillation Methods 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 4
239000000376 reactant Substances 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
RLWFMZKPPHHHCB-PWNYCUMCSA-N (1r,2r)-cyclopropane-1,2-dicarboxylic acid Chemical class OC(=O)[C@@H]1C[C@H]1C(O)=O RLWFMZKPPHHHCB-PWNYCUMCSA-N 0.000 claims 1
150000001942 cyclopropanes Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 8
JBDOTWVUXVXVDR-UHFFFAOYSA-N 3-azoniabicyclo[3.1.0]hexane-2-carboxylate Chemical compound OC(=O)C1NCC2CC12 JBDOTWVUXVXVDR-UHFFFAOYSA-N 0.000 abstract description 4
230000004071 biological effect Effects 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000001816 cooling Methods 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
229940124024 weight reducing agent Drugs 0.000 description 7
HGWUUOXXAIISDB-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2CC21 HGWUUOXXAIISDB-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910000091 aluminium hydride Inorganic materials 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WJXYUEOVOQGJGV-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1NCC2CC21 WJXYUEOVOQGJGV-UHFFFAOYSA-N 0.000 description 2
ZRMYHUFDVLRYPN-UHFFFAOYSA-N 3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)C2CC12 ZRMYHUFDVLRYPN-UHFFFAOYSA-N 0.000 description 2
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 2
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
SXLDHZFJMXLFJU-UHFFFAOYSA-N diethyl cyclopropane-1,2-dicarboxylate Chemical compound CCOC(=O)C1CC1C(=O)OCC SXLDHZFJMXLFJU-UHFFFAOYSA-N 0.000 description 2
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
230000006698 induction Effects 0.000 description 2
-1 lithium aluminium anhydride Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
ZRMYHUFDVLRYPN-WSOKHJQSSA-N (1s,5r)-3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)[C@@H]2C[C@H]12 ZRMYHUFDVLRYPN-WSOKHJQSSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
OQEHGZOASMRNJW-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane Chemical compound C1C2CC2CN1CC1=CC=CC=C1 OQEHGZOASMRNJW-UHFFFAOYSA-N 0.000 description 1
LEQKPQQOCKLKHK-UHFFFAOYSA-N 3-cyclohexylpiperidine Chemical group C1CCCCC1C1CNCCC1 LEQKPQQOCKLKHK-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
238000007605 air drying Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
OKUDBXZACZBZJE-UHFFFAOYSA-N bis(2-methoxyethoxy)aluminum;sodium Chemical compound [Na].COCCO[Al]OCCOC OKUDBXZACZBZJE-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
RLWFMZKPPHHHCB-UHFFFAOYSA-N cyclopropane-1,2-dicarboxylate;hydron Chemical compound OC(=O)C1CC1C(O)=O RLWFMZKPPHHHCB-UHFFFAOYSA-N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
SXLDHZFJMXLFJU-RNFRBKRXSA-N diethyl (1r,2r)-cyclopropane-1,2-dicarboxylate Chemical class CCOC(=O)[C@@H]1C[C@H]1C(=O)OCC SXLDHZFJMXLFJU-RNFRBKRXSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Landscapes

Indole Compounds (AREA)

CA381,217A 1978-07-06 1981-07-06 Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation Expired CA1127159A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA381,217A CA1127159A (fr)	1978-07-06	1981-07-06	Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/922,407 US4183857A (en)	1978-07-06	1978-07-06	3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione
US922,407		1978-07-06
CA000329751A CA1116612A (fr)	1978-07-06	1979-06-14	Procedes d'obtention de derives de 3-azabicyclo(3.1.0)hexane
CA381,217A CA1127159A (fr)	1978-07-06	1981-07-06	Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation

Publications (1)

Publication Number	Publication Date
CA1127159A true CA1127159A (fr)	1982-07-06

Family

ID=27166292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA381,217A Expired CA1127159A (fr)	1978-07-06	1981-07-06	Derives du 3-azabicyclo (3.1.0)hexane et methodes de preparation

Country Status (1)

Country	Link
CA (1)	CA1127159A (fr)

1981
- 1981-07-06 CA CA381,217A patent/CA1127159A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-07-06	MKEX	Expiry

Publication	Publication Date	Title
CA1116612A (fr)	1982-01-19	Procedes d'obtention de derives de 3-azabicyclo(3.1.0)hexane
SU470112A3 (ru)	1975-05-05	Способ получени производных 4-пиперидинола
DE69411243T2 (de)	1998-11-19	Verfahren zur herstellung eines lignan-derivats
JPH1192423A (ja)	1999-04-06	トリフルオロ酢酸及びクロロジフルオロ酢酸のメチルエステル又はエチルエステルの製造方法
JPH09235251A (ja)	1997-09-09	９，１０−エンドエタノ−９，１０−ジハイドロアントラセン−１１，１１−ジカルボン酸のモノエステルまたはジエステルの合成方法、この合成方法により得られる新規なモノエステルまたはジエステル、及びこれらの、均整または不整メチリデンマロネートの合成への応用
DE3688937T2 (de)	1994-01-20	Herstellung optisch aktiver aryloxypropanolamine und arylaethanolamine.
US4018824A (en)	1977-04-19	1-Aryloxy-3-aminopropane derivatives
Yamagiwa et al.	1978	Reactions of the α-carbanion species of (phenylthio) acetic acid and its ester with carbonyl compounds
DE69031780T2 (de)	1998-07-16	Verfahren zur Herstellung von (trans)-4-substituierten-DL-Prolinederivaten
WO1983002610A1 (fr)	1983-08-04	Derives de 3,3-dialkyle-indoline et de 3,3-alkylene-indoline, leur procede de fabrication et preparations pharmaceutiques les contenant
EP0366149B1 (fr)	1993-01-13	Procédé relatif à la synthèse de l'acide 3-chloro-2,4,5,trifluorobenzoique
DE2918900A1 (de)	1979-11-22	Verfahren zur herstellung von 1,5- dimethyl-bicyclo- eckige klammer auf 3,2,1 eckige klammer zu octanol-8 und dessen ester
US4496762A (en)	1985-01-29	Process for the preparation of N-(2-(cyclo-hexen-1-yl)ethyl)-4-methoxybenzeneacetamide
US4276218A (en)	1981-06-30	Preparation of dihalogenovinyl-γ-butyrolactones
US4925958A (en)	1990-05-15	Process for the preparation of N-alkoxycarbonylmethyl-N-formyl-amines and -anilines
EP0862548B1 (fr)	2003-04-02	Procedes de production de delta-lactones et d'acides hydroxyliques a partir d'acides gras insatures et leurs glycerides
EP0272981B1 (fr)	1990-11-14	Dérivés d'acide dibenzo[be]oxepinne-acétique, leur préparation et leur application en thérapeutique
JPH0131504B2 (fr)	1989-06-26
JP2880203B2 (ja)	1999-04-05	フラノン誘導体の製法
KR800000862B1 (ko)	1980-08-28	치환 인다닐-5-카복실산의 제조방법
SU810695A1 (ru)	1981-03-07	Способ получени 1,3-диоксанонов-4
JPH0317062A (ja)	1991-01-25	α―アミノ―ε―カプロラクタムの製造法
JPS5973544A (ja)	1984-04-25	レゾルシンの製法
CH313377A (fr)	1956-04-15	Procédé de préparation de nouveaux dérivés de la phénothiazine
Fujita et al.	1979	United States Patent:“