Ammonia → HCID 68147319, compound

Participants

Reaction Steps

At -78°, a mixture of 15 ml. of hydrogen fluoride and 5 ml. of N-methylpyrrolidone is combined successively with 5.1 g of 4,9(11)-androstadiene-3,17-dione and 10 g. of N-chlorosuccinimide. The reaction solution is allowed to stand for 2 days at +3° and then introduced into a mixture of ice/water and a 25% ammonia solution. The thus-precipitated product is worked up as set forth in Example A. After chromatography of the crude product on silica gel with acetone/hexane, 1.6 g. of 9-chloro-11β-fluoro-4-androstene-3,17-dione is isolated as an oil. UV: ε239 = 16,200 (methanol).

Provenance & Evidence