Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one

Abstract

Stereospecific transformations of 5α,6β-dichloroandrost-2-en-17-one into 3α-amino-2β-hydroxyandrost-5-en-17-one and 2β-amino-3α-hydroxyandrost-5-en-17-one have been achieved via the Δ⁵-2β,3β- and 2α,3α-epoxides. Direct treatment of the 5α,6β-dichloro-2β,3β-epoxide with sodium azide gave 3α,6α-bisazido-2βhydroxyandrost-4-en-17-one, while the 5α,6β-dichloro-2α,3α-epoxide gave 2β,6α-bisazido-3α-hydroxyandrost-4-en-17-one.