Synthesis and chemical behaviour of 17α-butyl-3β,17β-dihydroxy-16-oximino-5-androstene

Abstract

Starting from 3 -hydroxy-16-oximino-5-androsten-17-one (1), the recently synthesized 16-oximino-17 -hydroxy-17 -butyl derivative 2 gave by the Beckmann fragmentation reactionwith titanium(III) chloride or p-toluenesulphonyl chloride the corresponding D-seco derivative 3. However, using acetic anhydride, in addition to the 3 -acetoxy D-seco derivative 4, the 17-aza D-homo derivative 5 was obtained. The structure of compound 5 was proposed on the basis of NMR-spectroscopy.

Keywords

• 17-aza-d-homo derivatives of androstene
• beckmann fragmentation