Water → HCID 9901150, compound

Participants

Reaction Steps

A solution of 170 mg of product (C), obtained under 3a), in 22.5 ml of methanol was stirred with 300 mg of oxalic acid and 3 ml of water for 24 hours at room temperature. Then, it was mixed with sodium bicarbonate solution, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 62.7 mg of pure 11β-fluoro-17β-hydroxy-7α-methyl-estr-5(10)-en-3-one (I″) was obtained. Crystallization from hexane yielded 47.6 mg of compound I″ with a melting point of 169.9° C. ([α]D20=+134.4° (c=0.56% chloroform)).

Provenance & Evidence