Methanol → 3alpha-Hydroxy-2beta-methoxy-17beta-methoxycarbonyl-5alpha-androstan-11-one
Reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][C:16]1=[O:21])([CH3:14])[C@@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[CH3:26][OH:27].S(=O)(=O)(O)O>O>[OH:1][C@@H:3]1[C@@H:2]([O:27][CH3:26])[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C:16](=[O:21])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:22]([O:24][CH3:25])=[O:23])[CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one (500 mg.) in warm dry methanol (30 ml.) was treated with concentrated sulphuric acid (0.15 ml.). After 30 minutes the solution was poured into stirred water. The precipitated product was isolated, washed with water and dried over sodium hydroxide in vacuo to give fairly pure title compound (420 mg.) as a white powder; m.p. 170°-182°; [α]D + 68°,