Reductive decyanation of N-protected 6-Amino-3-azabicyclo[3.1.0]hexanecarbonitriles

Abstract

The cyano moiety in dibenzylamino-3-azabicyclo[3.1.0]hexane-6-carbonitriles 14c,d can be removed reductively by alkali metals: sodium in liquid ammonia at low temperatures causes a reaction with retention of configuration whilst lithium in an ethylamine - ammonia mixture at 0°C leads predominantly to inversion of configuration. The analogous diallylamino species 14e is less suitable for reductive decyanation. It can be used, however, for the synthesis of a 3-azabicyclo[3.2.0]heptane diamine 22. The solid state conformation of an N(3)-unsubstituted 3-azabicyclohexane skeleton is determined by an X-ray structural analysis.