Asymmetric Synthesis of cis-(S,R)-3-Amino-4-fluoro-1-methylpyrrolidine

Abstract

The development of the stereoselective synthesis of cis-(S,R)-3-amino-4-fluoro-1-methylpyrrolidine is described starting from chiral, non-racemic 1-[(3S,4S)-3-azido-4-hydroxypyrrolidin-1-yl]-2,2,2-trifluoroethan-1-one. Two sets of deoxyfluorination conditions are developed for achieving inversion of the chiral center with high or complete stereoselectivity.