20beta-Hydroxyprogesterone → HCID 57182055, compound

Participants

Reaction Steps

A solution of 34.8 g (0.11 mol) of (20R)-20-hydroxy-pregn-4-en-3-one in 300 ml of dimethyl sulphoxide is treated with 18.7 g (0.16 mol) of potassium tert. butoxide and stirred for 4 hours at room temperature under argon. The red-brown mixture is poured on to 1 kg of ice and the product is extracted with methylene chloride. The extract is washed with water, dried over sodium sulphate and evaporated in a water-jet vacuum. The residue is chromatographed on 1 kg of silica gel with hexane/ether/methylene chloride (7:2:1) and gives 7.3 g (21%) of uniform, crystalline (20R)-20-hydroxy-pregn-5-en-3-one. The analytical sample is obtained by recrystallisation from ethanol/methylene chloride; melting point 171°-175° C.; [α]D25 =-33.2° (c=0.5 in chloroform).

Provenance & Evidence