DD222015A5 - Verfahren zur herstellung von 1-substituierten azetidin-3-ol-derivaten - Google Patents

Verfahren zur herstellung von 1-substituierten azetidin-3-ol-derivaten Download PDF

Info

Publication number: DD222015A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; derivatives; acid halide; hal; aqueous medium
Prior art date: 1983-05-04

Application number

DD84262630A

Other languages

German (de)

English (en)

Inventor

Alexander F Orr

Original Assignee

Shell Int Research

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.)

1983-05-04

Filing date

1984-05-02

Publication date

1985-05-08

1984-05-02 Application filed by Shell Int Research filed Critical Shell Int Research

1985-05-08 Publication of DD222015A5 publication Critical patent/DD222015A5/de

Links

-1 1-SUBSTITUTED AZETIDINE-3-OL Chemical class 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title abstract 2
150000004820 halides Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 11
239000012736 aqueous medium Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
238000007363 ring formation reaction Methods 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
239000002585 base Substances 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000005826 halohydrocarbons Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
125000005002 aryl methyl group Chemical group 0.000 abstract description 2
GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical class OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 abstract description 2
230000008635 plant growth Effects 0.000 abstract description 2
239000004593 Epoxy Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical class OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XNPBVLLNKJHQAO-UHFFFAOYSA-N 1-(benzylamino)-3-chloropropan-2-ol Chemical compound ClCC(O)CNCC1=CC=CC=C1 XNPBVLLNKJHQAO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000736839 Chara Species 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
PBIUUJCEMUAWJJ-UHFFFAOYSA-N azetidine-3-carbonitrile Chemical class N#CC1CNC1 PBIUUJCEMUAWJJ-UHFFFAOYSA-N 0.000 description 1
150000001539 azetidines Chemical class 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 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
238000010828 elution Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000009993 protective function Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 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)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD84262630A 1983-05-04 1984-05-02 Verfahren zur herstellung von 1-substituierten azetidin-3-ol-derivaten DD222015A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838312104A GB8312104D0 (en)	1983-05-04	1983-05-04	Preparation of 1-substituted azetidin-3-ol derivatives

Publications (1)

Publication Number	Publication Date
DD222015A5 true DD222015A5 (de)	1985-05-08

Family

ID=10542093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84262630A DD222015A5 (de)	1983-05-04	1984-05-02	Verfahren zur herstellung von 1-substituierten azetidin-3-ol-derivaten

Country Status (17)

Country	Link
US (1)	US4560507A (cs)
EP (1)	EP0125714B1 (cs)
JP (1)	JPS59206350A (cs)
KR (1)	KR840009086A (cs)
AT (1)	ATE30718T1 (cs)
AU (1)	AU563050B2 (cs)
BR (1)	BR8402056A (cs)
CA (1)	CA1240685A (cs)
CS (1)	CS244813B2 (cs)
DD (1)	DD222015A5 (cs)
DE (1)	DE3467345D1 (cs)
ES (1)	ES8505947A1 (cs)
GB (1)	GB8312104D0 (cs)
HU (1)	HU191682B (cs)
IL (1)	IL71722A (cs)
SU (1)	SU1318156A3 (cs)
ZA (1)	ZA843258B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8412814D0 (en) *	1984-05-18	1984-06-27	Shell Int Research	1-substituted azetidine-3-ol derivatives
GB8419085D0 (en) *	1984-07-26	1984-08-30	Shell Int Research	Azetidine derivatives
GB8627493D0 (en) *	1986-11-18	1986-12-17	Shell Int Research	Catalytic hydrogenolysis
EP1158996A4 (en) *	1999-02-18	2005-01-12	Kaken Pharma Co Ltd	NEW AMIDE SECRETAGOGUES OF GROWTH HORMONE DERIVATIVES
WO2009091573A1 (en) *	2008-01-16	2009-07-23	Alcatel-Lucent Usa Inc.	Accessing networks for limited purposes
CN115385840B (zh) *	2022-09-05	2024-07-02	北京京宇复瑞科技集团有限责任公司	制备3-甲氧基氮杂环丁烷盐酸盐的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE934508C (de) *	1954-04-23	1955-10-27	Dehydag Gmbh	Verfahren zur Herstellung galvanischer Metallueberzuege
DE1111638B (de) *	1956-06-22	1961-07-27	Ernst Schneider Dipl Chem Dr R	Verfahren zur Herstellung von Trimethyleniminverbindungen
GB1236078A (en) *	1968-07-04	1971-06-16	Beecham Group Ltd	Substituted azetidinols
US3649618A (en) *	1970-10-02	1972-03-14	Abbott Lab	Certain 1-aralkyl azetidines
US4341887A (en) *	1980-03-07	1982-07-27	Petrolite Corporation	Azetidinium salts and polymers and copolymers thereof

1983
- 1983-05-04 GB GB838312104A patent/GB8312104D0/en active Pending
1984
- 1984-04-10 CA CA000451647A patent/CA1240685A/en not_active Expired
- 1984-04-13 AT AT84200534T patent/ATE30718T1/de not_active IP Right Cessation
- 1984-04-13 DE DE8484200534T patent/DE3467345D1/de not_active Expired
- 1984-04-13 EP EP84200534A patent/EP0125714B1/en not_active Expired
- 1984-04-27 US US06/604,696 patent/US4560507A/en not_active Expired - Fee Related
- 1984-05-02 CS CS843245A patent/CS244813B2/cs unknown
- 1984-05-02 DD DD84262630A patent/DD222015A5/de not_active IP Right Cessation
- 1984-05-02 ES ES532098A patent/ES8505947A1/es not_active Expired
- 1984-05-02 AU AU27586/84A patent/AU563050B2/en not_active Ceased
- 1984-05-02 ZA ZA843258A patent/ZA843258B/xx unknown
- 1984-05-02 BR BR8402056A patent/BR8402056A/pt not_active IP Right Cessation
- 1984-05-02 KR KR1019840002377A patent/KR840009086A/ko not_active Withdrawn
- 1984-05-02 JP JP59087982A patent/JPS59206350A/ja active Pending
- 1984-05-02 IL IL71722A patent/IL71722A/xx unknown
- 1984-05-02 HU HU841701A patent/HU191682B/hu not_active IP Right Cessation
- 1984-05-03 SU SU843735695A patent/SU1318156A3/ru active

Also Published As

Publication number	Publication date
IL71722A (en)	1987-12-20
EP0125714A1 (en)	1984-11-21
AU563050B2 (en)	1987-06-25
AU2758684A (en)	1984-11-08
ES532098A0 (es)	1985-06-16
DE3467345D1 (en)	1987-12-17
ES8505947A1 (es)	1985-06-16
SU1318156A3 (ru)	1987-06-15
US4560507A (en)	1985-12-24
ATE30718T1 (de)	1987-11-15
CS324584A2 (en)	1985-09-17
KR840009086A (ko)	1984-12-24
GB8312104D0 (en)	1983-06-08
JPS59206350A (ja)	1984-11-22
HUT34002A (en)	1985-01-28
ZA843258B (en)	1984-12-24
IL71722A0 (en)	1984-09-30
EP0125714B1 (en)	1987-11-11
BR8402056A (pt)	1984-12-11
HU191682B (en)	1987-03-30
CS244813B2 (en)	1986-08-14
CA1240685A (en)	1988-08-16

Legal Events

Date	Code	Title	Description
1994-07-21	ENJ	Ceased due to non-payment of renewal fee

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DE3601285C2 (cs)	1988-07-21
DE69313771T3 (de)	2002-04-18	Carbazolon - Derivate und Verfahren zu ihrer Herstellung
DD222015A5 (de)	1985-05-08	Verfahren zur herstellung von 1-substituierten azetidin-3-ol-derivaten
DE2205144C3 (de)	1982-02-11	Azetidino [3,2-d] thiazole und Verfahren zu ihrer Herstellung
DE1900514A1 (de)	1970-08-20	Verfahren zur Herstellung von Diisocyanaten
DE3026602C2 (cs)	1990-05-03
EP0161580A2 (de)	1985-11-21	Verfahren zur Herstellung eines Lactons
DE2433176C3 (de)	1979-06-07	N-Cyano-cyano-acetimidate und Verfahren zur Herstellung von 2-Halopyrinüdinderivaten
DE3850977T2 (de)	1994-12-15	Verfahren zur Herstellung von Azetidinonen.
CH634555A5 (de)	1983-02-15	Verfahren zur herstellung von mit nocardicin verwandten azetidinonen.
DE3150918C1 (de)	1983-04-21	Verfahren zur Herstellung von Aniliden in der Ergolinreihe
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DE3012667A1 (de)	1980-10-23	Verfahren zur herstellung von derivaten von 6- beta -amidinopenicillansaeure
DE2828888A1 (de)	1979-01-18	Verfahren zur herstellung von pyridincarbonsaeureamiden
DE4116157A1 (de)	1992-11-19	Verfahren zur herstellung von imidazothiazolon-derivaten
EP0224612A1 (de)	1987-06-10	Verfahren zur Herstellung von N-Cyano-N'-methyl-N"[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]guanidin
DE1695667A1 (de)	1971-06-16	Neue Pyrrolderivate,deren Herstellung und deren Verwendung
WO1991016304A1 (de)	1991-10-31	Verfahren zur herstellung von gramin-derivaten
DE3707530A1 (de)	1987-09-17	Neue substituierte dihalogenpyridine und verfahren zu ihrer herstellung sowie ihre weitere umsetzung zu pyridindicarbonsaeurediestern
AT358171B (de)	1980-08-25	Verfahren zur herstellung von neuen rifamycin- -verbindungen
DE3208656A1 (de)	1982-10-21	Verfahren zur herstellung von 11-(2'-substituierten)acetyl-5,11-dihydro-6h-pyrido-(2,3-b) (1,4)-benzodiazepin-6-onen und deren pharmazeutisch vertraeglichen salzen
AT339912B (de)	1977-11-10	Verfahren zur herstellung von neuen azetidinverbindungen
DE4024692A1 (de)	1992-02-06	Verfahren zur herstellung von cyanhydantoinen