Dimethyl Sulfoxide → HCID 13421129, compound

Participants

Reaction Steps

To a solution of (11β,17β)-11-(acetyloxy)-9-fluoro-17-hydroxyandrosta-1,4-dien-3-one (1.6 g, 4.42 mmole) in dry dimethylsulfoxide (30 ml), acetic acid (10 ml) and acetic anhydride (20 ml) were added. The starting steroid disappeared in 20 hours. The mixture was added into water and was extracted with chloroform (3×100 ml). The chloroform extracts were combined, washed with dilute brine and water, dried (anhydrous magnesium sulfate) and was evaporated in vacuo. The residue was dissolved in chloroform-hexane (1:1) and was absorbed on a column of silica gel (45 g). Elutions of the column successively with the same solvent mixture, chloroform and chloroform-ethyl acetate mixtures (2,3,5 and 10% ethyl acetate) gave (i) the homogeneous (tlc) title compound (1.1 g), (ii) a mixture of the 17α-isomer of the title compound and (11β)-11-(acetyloxy)-9-fluoroandrosta-1,4-dien-3,17-dione (300 mg), and (iii) (11β)-11-(acetyloxy)-9-fluoroandrosta-1,4-dien-3,17-dione (280 mg).

Provenance & Evidence