Hydrogen Peroxide → 1alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one
Reaction equation
[CH3:1][O:2][CH:3]([O:26][CH3:27])[CH:4]([CH3:25])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH:15]=[CH:16]2)[CH:11]=[CH:10]3)[CH2:7][CH2:6]1.[OH-:28].[Na+].OO>CO>[O:28]1[C@H:15]2[C:14](=[O:24])[CH:13]=[C:12]3[C@:17]([CH3:18])([C@@H:16]12)[C@@H:19]1[C@H:9]([C@H:8]2[C@:22]([CH3:23])([CH2:21][CH2:20]1)[C@@H:5]([CH:4]([CH3:25])[CH:3]([O:2][CH3:1])[O:26][CH3:27])[CH2:6][CH2:7]2)[CH:10]=[CH:11]3Participants
5
Procedure
To a solution of 2.00 g (5.4 mmoles) of 21,21-dimethoxy-20-methylpregna-1,4,6-trien-3-one in 70 ml of methanol were added a 10 wt % solution of sodium hydroxide in methanol (0.55 ml) and 3.04 ml of a 30 wt. % aqueous solution of hydrogen peroxide (containing 29.8 mmoles of hydrogen peroxide) and the mixture was stirred at room temperature for 14 hours. The reaction mixture was worked up in the same manner as Example 6 to recover 1.56 g of 1α,2α-epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one (yield: 75%).
Sources & evidence
- ORD record
- ord-90129d85df064de692f74da5d323b97d
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112998
Reaction notes
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