Hydrogen Peroxide → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

HRID 1196313Notes

Reaction equation

HRID 1196313 reaction equation
[OH-].[Na+].OO.[CH3:5][C:6]1([CH3:34])[CH2:11][O:10][CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C@H:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21](=[CH:22][C:23](=[O:33])[CH:24]=[CH:25]3)[CH:20]=[CH:19]4)[CH2:16][CH2:15]2)[CH3:13])[O:8][CH2:7]1.C(OCC)(=[O:37])C.CCCCCC>CO.O>[CH3:34][C:6]1([CH3:5])[CH2:7][O:8][CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C@H:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21](=[CH:22][C:23](=[O:33])[C@@H:24]5[O:37][C@@H:25]53)[CH:20]=[CH:19]4)[CH2:16][CH2:15]2)[CH3:13])[O:10][CH2:11]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one

Product 1

HCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-oneYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

A 10 weight % solution of sodium hydroxide in methanol (1.16 ml) and 6.36 ml of a 30 weight % solution of hydrogen peroxide in water (containing 62.3 mmoles of hydrogen peroxide) were added to a solution of 4.66 g (11.3 mmoles) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one in 150 ml of methanol and the mixture was stirred at room temperature for 16 hours. The reaction mixture thus obtained was diluted with water and after the methanol was partially distilled off under reduced pressure at room temperature, the residue was extracted with ether. The extract was washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution and the organic layer was dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1:10, v/v) to recover 3.72 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one (yield: 77%).

Workup

  1. customThe reaction mixture thus obtained
  2. distillationafter the methanol was partially distilled off under reduced pressure at room temperature
  3. extractionthe residue was extracted with ether
  4. washThe extract was washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-6d7909af6ace465cb48f8d3d6c5a4501
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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