Abstract
4β,5-Epoxy-5β-androstane-3,17-dione ( 1a ), 17β-hydroxy-4β,5-epoxy-5β-androstan-3-one ( 1b ) and 17β-acetoxy-4β,5-epoxy-5β-androstan-3-one ( 1c ) were treated with anhydrous hydrogen fluoride in pyridine (70% solution) at 55° and yielded the corresponding 4-en-4-ols e.g. 4-hydroxy-4-androstene-3, 17-dione ( 2a ). As the reaction temperature was lowered each epoxide formed a second product which, at −75°, was the major component of the reaction mixture and was identified as the 5α-fluoro-4α-ol derivative of the parent enone, e.g. 4α-hydroxy-5-fluoro-5α-androstane-3,17-dione ( 3a ). These fluorohydrins are thermally unstable, losing hydrogen fluoride. The acetates of the fluorohydrins were also prepared, characterized, and shown to be more stable than the parent alcohols.
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