Synthesis of some 9-benzyl-8-azabicyclo[4.3.0]nonan-7-ones

Abstract

A route to cis,cis-9-benzyl-8-azabicyclo[4.3.0]nonan-7-one, based on the reaction of benzylmagnesium chloride with N-benzyl-cis-hexahydrophthalimide and in which N-benzyl-9-benzylidene-8-azabicyclo[4.3.0]nonan-7-one is a key intermediate, is described, and the introduction of carbon and oxygen substituents at C-6 of 8,9-dibenzyl-8-azabicyclo[4.3.0]nonan-7-one is reported. The preparation and some reactions of the cis,cis,cis- and trans,cis,trans-forms of N-benzyl-5-hydroxymethyl-2-methyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione are also described.