Sodium Chloride → 11beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

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Reaction Steps

A solution of 466 mg of 7α-(5-bromopentyl)-11β-fluorooestra-1,3,5(10)-triene-3,17-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred at a bath temperature of 80° C. for 3 hours with 1.0 g of methyl-(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amine. For work-up, the mixture is added to saturated sodium chloride solution, extracted with ether, dried over sodium sulphate, concentrated in vacuo and the residue is chromatographed on silica gel using ethyl acetate/methanol. 546 mg of 11β-fluoro-7α-{5-[methyl-(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-oestra-1,3,5(10)triene-3, 17β-diol are obtained as a foam, [α]D=+39° (c=0.5 in CHCl3)

Provenance & Evidence