m-Chloroperbenzoic acid → 6alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3-one

HRID 1196352Notes

Reaction equation

HRID 1196352 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]1[C@H:14]2[C:15](=[O:39])[CH:16]=[C:17]3[C@:36]([CH3:37])([C@@H:13]12)[C@@H:35]1[C@H:20]([C@H:21]2[C@:32]([CH3:38])([CH2:33][CH2:34]1)[C@@H:24]([CH:25]([CH3:31])[CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH2:23][CH2:22]2)[CH:19]=[CH:18]3>C(Cl)(Cl)Cl>[O:12]1[C:14]2=[C:13]3[C@:36]([CH3:37])([CH2:17][CH2:16][C:15]2=[O:39])[C@@H:35]2[C@H:20]([C@H:21]4[C@:32]([CH3:38])([CH2:33][CH2:34]2)[C@@H:24]([CH:25]([CH3:31])[CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH2:23][CH2:22]4)[C@@H:19]2[O:9][C@:18]123

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 540033941alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one

Product 1

HCID 867458216alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3-oneYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 0.836 g (0.5 mmole) of m-chloroperbenzoic acid and 70 ml of chloroform was added to a mixture of 0.772 g (2.0 mmoles) of 1α,2α-epoxy-21,21-dimethoxy-20-methylpregna-4,6-dien-3-one and 20 ml of chloroform and the whole mixture was stirred at room temperature for 1 day. The reaction mixture thus obtained was worked up in the same manner as Example 7 to recover 0.498 g of 1α,2α;6α,7α-diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3-one (yield: 62%).

Workup

  1. customThe reaction mixture thus obtained
  2. customto recover 0.498 g of 1α,2α

Sources & evidence

ORD record
ord-b5a004403c894310a5ca4ec0b99d80e9
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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