Abstract: The process for the preparation of chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines used as key intermediates for the preparation of naphthyridine and quinolone antibacterial agents which comprises reacting readily available chiral 1-substituted-3-pyrrolidinols to their corresponding chiral sulfonate esters; converting the sulfonate esters to chiral 1-substituted-3-cyanopyrrolidines having an inverse configuration, and then dialkylating the chiral cyanopyrrolidines with alkyl lithium in the presence of a Lewis acid without racemization at the asymmetric carbon atom is described.
Type:
Grant
Filed:
July 7, 1993
Date of Patent:
September 13, 1994
Assignee:
Warner-Lambert Company
Inventors:
Victor Fedij, Mark J. Suto, James N. Wemple, James R. Zeller