Pfizer Corporation

Dsm Pharmaceuticals, Inc.

Thomas C Nugent

Robert Seemayer

Jack S Liang

The present invention is directed to a process for preparing (S,S)-cis-2-phenyl-3-aminopiperidine and (S,S)-cis-2-phenyl-3-tertbutoxycarbonylaminopiperidine.

Process for the preparation of (S,S)-cis-2-phenyl-3-aminopiperidine

A process for preparing (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. The process includes the steps of contacting a compound containing a mixture of R- and S-isomers and having the formulawith an effective amount of a chiral organic acid in the presence of an organic solvent and an effective amount of an organic carboxylic acid for converting the R-isomer into an acid salt of the S isomer, wherein the organic solvent is capable of solubilizing the compound containing the mixture of R- and S-isomers, while precipitating the acid salt and the organic carboxylic acid is different from the chiral organic acid; neutralizing the acid salt with a base to provide an S-isomer of a chiral ketone of the formula; and reacting the chiral ketone with an organic amine in the presence of a Lewis acid to provide the corresponding imine and reducing the imine.

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San Francisco, CA, United States of America

Thomas C Nugent