Synthesis and Reaction of 1-Azabicyclo [3.1. 0] hexane

K Hayashi, E Kujime, H Katayama, S Sano…

Index: Hayashi, Kazuhiko; Kujime, Eiko; Katayama, Hajime; Sano, Shigeki; Shiro, Motoo; Nagao, Yoshimitsu Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 10 p. 1142 - 1146

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Citation Number: 7

Abstract

The effective formation of 1-azabicyclo [3.1. 0] hexane (5) by treatment of 2-(bromomethyl) pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on intermolecular Br··· Li+ coordination (SN2 process). The reaction of 5 with electrophiles 13a—n gave the corresponding pyrrolidines 14a—n and piperidine 6, 15a—g, i—n. The selectivity of the ...