m-Chloroperbenzoic acid → 20,20-Ethylenedioxy-2alpha,3alpha-epoxy-5alpha-pregnan-11-one

HRID 1701457Notes

Reaction equation

HRID 1701457 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]1[CH2:37][O:36][C:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C@H:20]4[C@H:30]([C:31](=[O:35])[CH2:32]3)[C@:28]3([CH3:29])[C@H:23]([CH2:24][CH:25]=[CH:26][CH2:27]3)[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)([CH3:15])[O:13]1>>[CH2:37]1[CH2:12][O:13][C:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C@H:20]4[C@H:30]([C:31](=[O:35])[CH2:32]3)[C@:28]3([CH3:29])[C@H:23]([CH2:24][C@@H:25]5[O:6][C@@H:26]5[CH2:27]3)[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)([CH3:15])[O:36]1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70583481HCID 70583481, compound

Product 1

HCID 8673688320,20-Ethylenedioxy-2alpha,3alpha-epoxy-5alpha-pregnan-11-oneYield 86.9%

Procedure

85%-m-Chloroperoxybenzoic acid (14.74 g) was added to a stirred solution of 20,20-ethylenedioxy-5α-pregn-2-en-11-one (26.0 g) at 20° to 25° during 15 minutes. After 45 minutes the solution was washed with 5% sodium hydrogen carbonate solution (2×300 ml) and water (300 ml). Evaporation of the solvent and crystallisation of the residue from 1% pyridine in methanol (300 ml) gave the title compound (23.6 g) m.p. 159°-160°.

Workup

  1. washAfter 45 minutes the solution was washed with 5% sodium hydrogen carbonate solution (2×300 ml) and water (300 ml)
  2. customEvaporation of the solvent and crystallisation of the residue from 1% pyridine in methanol (300 ml)

Sources & evidence

ORD record
ord-27658111928c497fab67feb4e56374ac
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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