Patent ID: 6914142
Filing Date: 2005-07-05
Classification: C07D

Abstract:
1. A process for preparing a compound of Formula VII: wherein said compound is in its Z-isomer form in at least about 90% stereochemical purity and “Acid” refers to acid salt, said process comprising: (a) converting isonipecotic acid (Formula III) to its N-protected derivative (Formula IIIA): where Y is a protecting group; (b) converting the compound of Formula IIIA to its acid halide (Formula IV): (c) reacting said compound of Formula IV with a suitable halobenzene in the presence of a suitable Friedel-Crafts catalyst to yield the compound of Formula V: where X is a halogen; (d) reacting the compound of Formula V with an alkoxyamine and an acid, to provide the compound of Formula VI as a mixture of the Z and E isomers: and (e) isomerizing the compound of Formula VI by treatment with a strong acid and simultaneously converting to the desired acid salt of Formula VII with an enriched Z isomer, wherein the Z isomer predominates over the E-isomer by at least about a 90:10 ratio.