A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

Abstract

Azetidines and their derivatives are of major interest since they exhibit important biological activities besides their utility as synthetic intermediates. Herein we describe a mild and efficient method for the formation of functionalized N-alkyl-azetidines in moderate-to-good yields starting from 1,2-aminoalcohols. This azetidine synthesis proceeds through three steps involving O-methylation of the starting 1,2-amino alcohols, reduction of the ester group of the resulting 1,2-aminoethers, and subsequent mesylation/intracyclization of the 1,3amino alcohol intermediates.