Process for the enantioselection synthesis of alkylated...

Details Process for the enantioselection synthesis of alkylated... Process for the enantioselection synthesis of alkylated...

C - Chemistry, Metallurgy

07

D

260/319.2

C07D 209/34 (2006.01)

Patent

CA 2034668

ABSTRACT: - 1 - HOE 90/S 002 Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (?)-1,3- dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)- 1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

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