(Diethylamino)sulfur trifluoride → HCID 18647601, compound

Participants

Reaction Steps

A solution of methyl 3α-tert-butyldimethylsilyloxy-6α-hydroxy-7-keto-5β-cholanoate (2.4 g, 4.49 mmoles) in methylene chloride (50 ml) was added dropwise in one hour to a solution of diethylamino-sulfur-trifluoride (2.72 ml, 20.0 mmoles) in methylene chloride (50 ml) and the mixture was left to react overnight under argon atmosphere, with magnetic stirring. The reaction mixture was washed with water (1×30 ml), subsequently with a sodium bicarbonate saturated solution (2×20 ml), finally with brine (1×30 ml). The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue (2.0 g) was subjected to flash chromatography on silica, eluting with methylene chloride, to obtain 0.6 g of a pure product (32%).

Provenance & Evidence