p-Toluenesulfonic acid → HCID 69905541, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2β-isopropoxy-3α-hydroxy-5α-androstan-17-one tosylhydazone (300 mg), NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added DMF and sulfolane (1:1, 3 mL) and the mixture obtained was heated to 110° C. for 3 h. Then additional amount of NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added and it was heated for another hour. Water was then added and the mixture was extracted with EtOAc (2×45 mL). The combined extracts were dried over Na2SO4 and the crude product obtained by removal of the solvent was purified by flash chromatography over silica gel to yield the pure 2β-isopropoxy-3α-hydroxy-5α-androstane (37 mg); TLC Rf (EtOAc:hexane 1:9)=0.17.

Provenance & Evidence