p-Toluenesulfonic acid → HCID 86738594, compound

Participants

Reaction Steps

Toluene-4-sulphonic acid (570 mg) was added to a solution of methyl 11α-amino-5α-androst-2-ene-17β-carboxylate (1.0 g) in 1,2-dichloroethane (25 ml). After 0.5 h m-chloroperoxybenzoic acid (810 mg) was added and the mixture was left for a further 2 h. The mixture was washed with NaHSO3 solution, 5% NaHCO3 solution and water. The aqueous phases were extracted with dichloromethane and the combined organic phase was dried and evaporated to leave a foam which was purified by preparative t.l.c. in MeOH: 0.88 NH3 (50:1) to give the title compound (369 mg) as a foam [α]D +44°, νmax 1722 cm-1.

Provenance & Evidence