Formation of 18-nor-13(14)-ene-17β-methyl steroids during perfluoroacylation of anabolic steroids bearing a tertiary 17-hydroxy group and compounds related to corticosteroids

Abstract

The results of derivatization (for gas chromatography–mass spectrometry) of steroids bearing a tertiary 17-hydroxy group with perfluoroacyl anhydrides in acetone are presented. The reaction products are investigated by using low- and high-resolution mass spectrometry, metastable ion measurements, and proton and carbon-13 nuclear magnetic resonance spectroscopy. On the basis of the results, we conclude that all the products lose the 17-hydroxy group during derivatization and undergo a Wagner–Meerwein rearrangement to give 18-nor-13(14)-ene-17β-methyl steroids.