Warner-Lambert Company

James Guy Davidson, Iii

Ji Zhang

Peter Garth Blazecka

Brian S Swierenga

The invention relates to a process for preparing highly functionalized &#x3b3;-butyrolactams and &#x3b3;-amino acids by reductive amination of mucohalic acid or its derivatives, and discloses a process for preparing pregabalin, a GABA analog with desirable medicinal activity.

Process for preparing highly functionalized &#x3b3;-butyrolactams and &#x3b3;-amino acids

Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halo, halo-substituted alkyl, alkyl, cycloalkyl, aralkyl, aryl, heterocyclic, alkoxy, alkaryl, aryloxy, thioalkoxy, nitro, or N,N-dialkylamino are prepared by reacting 1-bromo-4-(trifluoromethyl)benzene with n-butyl lithium; reacting the product with a benzaldehyde of the formula: ##STR2## to produce a novel intermediate such as lithium 4-(trifluoromethyl)-.alpha.-]4-(trifluoromethyl)phenyl]benzenemethanol, and then reacting the lithium product with an acid or acid salt.

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Howell, MI, United States of America

James Guy Davidson, Iii