C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
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.
Mccague Raymond
Wang Shouming
Borden Ladner Gervais Llp
Darwin Discovery Limited
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