Steroids and related studies. Part 41. Schmidt reaction with 3β-acetoxypregn-5-ene-7,20-dione

Abstract

Treatment of 3β-acetoxypregn-5-ene-7,20-dione (1) with hydrazoic acid–boron trifluoride in chloroform gives a complex mixture. The major product is 17β-(5-methyltetrazol-1 -yl)-7a-aza-B-homoandrost-5-eno[7a,7-d]-tetrazol-3β-ol (5), followed by 17β-acetamido-7a-aza-B-homoandrost-5-eno[7a,7-d]tetrazol-3β-ol (8). Other products are 3β-hydroxy-7a-aza-B-homopregn-5-eno-[7a,7-d]tetrazol-20-one (6), pregna-3,5-diene-7,20-dione (2), and 17β-(5-methyltetrazol-1-yl)androsta-3,5-dien-7-one (3).