Preparation and reactions of some 1-cyano-steroids

Abstract

Some 1-cyano-steroids were prepared in unsuccessful attempts to form the corresponding 1-carboxy-steroids. Hydrolysis of 1 α-cyano-5α-cholestan-3-one produced the lactam of 3α-amino-3β-hydroxy-5α-cholestane-1α-carboxylic acid, while hydrolysis of the epimeric 1β-cyano-ketone produced the same lactam as a result of epimerisation at carbon-1. Reduction products of the 1-cyano-ketones are described and also the chemical shifts in n.m.r. signals resulting from the introduction of 1-cyano-substituents. Rotatory dispersion data on some cyano-substituted steroidal ketones are also listed.