Hydrogen Peroxide → HCID 86738157, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.79 g (8.92 mmol) of (20R)-20-hydroxy-pregna-1,4,6-trien-3-one in 27 ml of methanol is treated with 0.83 ml of 10% methanolic sodium hydroxide, cooled to 0° C., and 5.4 ml of 30% hydrogen peroxide solution are added dropwise during 10 minutes with stirring. The solution is stirred at 0° C. for 45 minutes and then at room temperature for 3 hours. The suspension formed is treated with a total of 60 ml of water in portions, cooled to 0° C. and excess peroxide is destroyed by the addition of sodium hydrogen sulphite solution. The mixture is freed from methanol in a water-jet vacuum and the residue is extracted with ethyl acetate. The extract is washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated. Chromatography of the residue on 80 g of silica gel with hexane/ether (1:1) gives 1.77 g (60.4%) of uniform (20R)-1α,2α -epoxy-20-hydroxy-pregna-4,6-dien-3-one in the form of colourless crystals. The analytical sample is obtained by recrystallisation from methylene chloride/ether; melting point 206°-207° C., [α]D25 =+231.6° (c=0.5 in chloroform); UV (ethanol): λmax 292 nm (ε=21050).

Provenance & Evidence