Hydrochloric Acid → HCID 68146606, compound

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Reaction Steps

A solution of 1.8 g. of 17β-acetoxy-11β-fluoro-4-androsten-3-one in 60 ml. of acetone and 12 ml. of water is combined with 2.6 g. of N-chlorosuccinimide; the reaction mixture is allowed to stand for 1 day at room temperature. Then, the solution is diluted with methylene chloride, washed successively with sodium thiosulfate solution and water, and dried over sodium sulfate. Chromatography of the crude product on silica gel with acetone/hexane yields 1.1 g. of 17β-acetoxy-6β-chloro-11β-fluoro-4-androsten-3-one. This product is dissolved in 100 ml. of chloroform and combined with 6 ml. of glacial acetic acid saturated with gaseous hydrogen chloride. The solution is allowed to stand at 0° for 2 hours and then introduced into ice/water. The precipitate is vacuum-filtered, washed with water, and dried. After purification by means of preparative layer chromatography (hexane/ethyl acetate 7 : 3), 530 mg. of 17β-acetoxy-6α-chloro-11β-fluoro-4-androsten-3-one is isolated as an oil. UV: ε236 = 15,400 (methanol).

Provenance & Evidence