Synthesis and chemical behaviour of 17a-butyl-3b,17b-dihydroxy-16-oximino-5-androstene (NOTE)

Abstract

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

Keywords

• 17-aza-D-homo derivatives of androstene
• Beckmann fragmentation