Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes

Abstract

Condensation of 2α,3α- and 2β,3β-epoxy-5α-androstanes with secondary cyclic amines gives 2β-amino-3α-ols and 3α-amino-2β-ols respectively; reaction of a 2β-bromo-3α-hydroxy-5α-androstane with the same cyclic amines gives the 2α,3α-epoxide in contrast to the 3α-bromo-2β-hydroxy-isomer, which undergoes substitution without inversion to give the corresponding 3α-amino-2β-ol. The mechanisms of these reactions are discussed. The preparation of 2-morpholino-5α-androst-1-ene-3,17-dione is also described.