Synthesis of an azaspirane via Birch reduction alkylation prompted by suggestions from a computer program

With the aid of proposals from a computer program for synthesis design, a new method of synthesizing azaspiranes has been developed. In this method, one starts with a suitable benzoic acid ester, which is subjected to Birch reduction. Then the anionic intermediate is alkylated with 1,2-dibromoethane. The product is subsequently reacted with an amine to give a spiro lactam.