Potassium Carbonate → 11beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

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Reaction Steps

500 mg of 11β-fluoro-3-hydroxy-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 15 ml of ethylmethylketone, mixed with 1.1 g of potassium carbonate and 1.5 ml of 1,1,1,2,2-pentafluor-5-iodo-pentane and refluxed for 2.5 hours. For working-up, the reaction mixture is cooled to room temperature, stirred into saturated common salt solution, extracted with ethyl acetate, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative column chromatography on silica gel with a methylene chloride-methanol gradient provides 397 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one.

Provenance & Evidence