Sodium periodate → 3-alpha,12-alpha-Diacetoxypregnan-20-one

Participants

Reaction Steps

To a solution of the crude 3α, 12α-diacetoxy-17β-[(1,1-diphenyl)-1,4-pentadien-4-yl]-5β-androstane (43.6 g) in carbon tetrachloride (110 ml), acetonitrile (110 ml) and water (146 ml) is added sodium periodate (46.8 g) and ruthenium(III) chloride hydrate (0.373 g). The mixture is stirred vigorously at room temperature for about 1 hour, sodium periodate (5.0 g) and ruthenium(III) chloride hydrate (0.10 g) are added and stirring continued for about 30 minutes. The mixture is diluted with methylene chloride, washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 5% ether in methylene chloride and further purified by flash chromatography in 25% ethyl acetate in hexane to give the desired product.

Provenance & Evidence