Amino-steroids. Part IV. 16β-Morpholino-17-oxo- and 17β-morpholino-16-oxo-5α-androstanes

Abstract

Condensation of a 17β-acetoxy-16α,17α-epoxy-5α-androstane with morpholine yields a 17β-morpholino-16-ketone as the major product, contaminated with some isomeric 16β-morpholino-17-ketone; in the presence of water the condensation yields the latter isomer as the major product. An intermediate in these reactions was shown to be a 16α-hydroxy-17-ketone. The mechanisms of these reactions are discussed and also those of the condensations of 16α-acetoxy-17-ketone, 17β-acetoxy-16-ketone, and 17β-hydroxy-16-ketone systems with morpholine to give 16β-morpholino-17-ketones.