“Enamine” Derivatives of Steroidal Carbonyl Compounds. II

Abstract

Steroidal C3-ketones have been shown to condense readily with pyrrolidine to form 3-(N-pyrrolidyl) enamines. In those polyketonic steroids having carbonyl groups in the C3-position and elsewhere in the molecule the reaction was selective on the three position leaving the other functional groups unprotected and available for further study. Testosterone was readily prepared by the lithium aluminum hydride reduction of the C3-(N-pyrrolidyl)-3,5-androstadien-17-one obtained thus from 4-androstene-3,17-dione. © 1953, American Chemical Society. All rights reserved.