Chiral nitriles, their preparation and their use for the...

C - Chemistry – Metallurgy – 07 – C

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C07C 255/43 (2006.01) C07C 253/30 (2006.01) C07C 253/34 (2006.01)

Patent

CA 2171431

A process for preparing a substantially single enantiomer (R or S) of R'-NH- (CH2)3-C(Ar) (CN)-R, the process comprising reacting together R-CH(Ar)-CN and X-(CH2)3-A to give X-(CH2)3-CH(Ar) (CN)-R, reacting that with methylamine to give R'-NH-(CH2)3-C(Ar) (CN)-R, and resolving that into a substantially single enantiomer thereof, wherein Ar is aryl, R and R' are each independently C1-20 alkyl, X is a halo atom and A is a leaving group and the resolution is carried out using a chiral acid. The process is particularly useful for preparing verapamil, and analogues thereof, in single enantiomeric form.

L'invention se rapporte à un procédé de préparation d'un énantiomère sensiblement simple (R ou S) de R'-NH- (CH¿2?)¿3?-C(Ar) (CN)-R, ce procédé consistant à faire réagir ensemble R-Ch(Ar)-Cn et X-(CH¿2?)¿3?-A, pour donner X-(CH¿2?)¿3?-CH(Ar) (CN)-R, que l'on fait réagir avec méthylamine pour donner R'-NH-(CH¿2?)¿3?-C-(Ar) (CN)-R, que l'on résout dans un énantiomère sensiblement simple de celui-ci, dans lequel Ar est aryle, R et R' sont chacun indépendamment alcoyle C¿1-20?, X est un atome d'halogène et A est un groupe labile, cette résolution s'effectuant en utilisant un acide chiral. Ce procédé est particulièrement utile dans la préparation de vérapamil et de ses analogues, sous forme énantiomorphe simple.

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