Tetrabutylammonium Fluoride → 11beta-Fluoro-7alpha-{5-[(3-hydroxypropyl)methylamino]-pentyl}oestra-1,3,5(10)-trien-17-one

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Reaction Steps

2.3 g of 11β-fluoro-7α-{5-[(3-tert-butyldimethylsilyl-oxypropyl)methylamino]pentyl}-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one in 23 ml of tetra-hydrofuran are reacted at room temperature with 6 ml of tetrabutylammonium fluoride solution (1M in tetra-hydrofuran). After 2 hours, the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated in vacuo. Chromatography of the crude product on silica gel using a methylene chloride-methanol gradient affords 1.5 g of 11β-fluoro-7α-{5-[(3-hydroxypropyl)methylamino]-pentyl}oestra-1,3,5(10)-trien-17-one as a foam.

Provenance & Evidence