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1. WO1997029080 - RACEMISATION OF QUATERNARY CHIRAL CENTERS

Publication Number WO/1997/029080
Publication Date 14.08.1997
International Application No. PCT/GB1997/000371
International Filing Date 10.02.1997
Chapter 2 Demand Filed 02.09.1997
IPC
C07B 55/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
55Racemisation; Complete or partial inversion
C07C 253/30 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
253Preparation of carboxylic acid nitriles
30by reactions not involving the formation of cyano groups
C07D 211/88 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
211Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
04with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
80having two double bonds between ring members or between ring members and non-ring members
84with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
86Oxygen atoms
88attached in positions 2 and 6, e.g. glutarimide
CPC
C07B 55/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
55Racemisation; Complete or partial inversion
C07C 253/30
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
253Preparation of carboxylic acid nitriles
30by reactions not involving the formation of cyano groups
C07D 211/88
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
211Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
04with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
80having two double bonds between ring members or between ring members and non-ring members
84with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
86Oxygen atoms
88attached in positions 2 and 6, e.g. glutarimide
Applicants
  • DARWIN DISCOVERY LIMITED [GB]/[GB] (AllExceptUS)
  • McCAGUE, Raymond [GB]/[GB] (UsOnly)
Inventors
  • McCAGUE, Raymond
Agents
  • GILL JENNINGS & EVERY
Priority Data
9602516.808.02.1996GB
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) RACEMISATION OF QUATERNARY CHIRAL CENTERS
(FR) RACEMISATION DE CENTRES CHIRAUX QUATERNAIRES
Abstract
(EN)
A process for the racemisation of an enantiomerically-enriched compound of the formula (3): X-(Ar)(Ak)C-(CH2)2-Y, comprises treatment of enantiomerically-enriched (3) with a base to obtain anion (4), optionally in protonated form, which is then combined with CH2=CH-Y1 to form racemic (3), wherein Ar = aryl or heteroaryl; Ak = C1-20 alkyl; X = CN, CO2R, CONR1R2, COR; Y and Y1 are independently selected from CN, CO2R, CONR1R2 and COR; and R, R1 and R2 are independently selected from H and C1-20 alkyl; optionally as a salt thereof. This racemisation process can be used as part of an efficient synthesis of enantiomerically-enriched verapamil or aminoglutethimide.
(FR)
L'invention concerne un procédé de racémisation d'un composé enrichi de manière énantiomère de la formule (3): X-(Ar)(Ak)C-(CH2)2-Y comprenant le traitement du composé enrichi de manière énantiomère (3) avec une base afin d'obtenir un anion (4), éventuellement sous forme protonée, qui est ensuite combiné à CH2=CH-Y1 afin d'obtenir un racémique (3); dans lesdites formules Ar = aryle ou hétéroaryle, Ak = alkyle C1-20, X = CN, CO2R, CONR1R2, COR, Y et Y1 sont sélectionnés indépendemment parmi CN, CO2R, CONR1R2 et COR, et R, R1 et R2 sont sélectionnés indépendemment entre H et alkyle C1-20; éventuellement sous forme d'un sel de ce composé. Ce procédé de racémisation peut être utilisé comme étape d'une synthèse efficace de vérapamil ou d'aminoglutéthimide enrichis de manière énantiomère.
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