4-Nitrobenzenecarboperoxoic acid → HCID 86743414, compound

Participants

Reaction Steps

36.0 g of 15α-propenyl-17β-hydroxy-1α-methyl-3α-tetrahydropyranyloxy-5α-androstane (German Laid-Open Application 35 39 244, Example 15a) is dissolved in 900 ml of ethylene chloride, combined with 63.0 g of p-nitroperbenzoic acid, and stirred for one hour at 0°-5° C. After dilution with methylene chloride, the mixture is washed with 1-molar sodium hydroxide solution and with water, and evaporated under vacuum. By chromatography on silica gel and crystallization from ether-pentane, 27.7 g of 17β-hydroxy-15α-(1,2-epoxypropyl)-1α-methyl-3α-tetrahydropyranyloxy-5α-androstane is produced, mp 172°-174° C.

Provenance & Evidence