m-Chloroperbenzoic acid → 6alpha,7alpha-Diepoxypregn-4-en-3one

HRID 1196314Notes

Reaction equation

HRID 1196314 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=O)C=1.CC1(C)CO[CH:16]([CH:19]([C@@H:21]2[C@:38]3([CH3:39])[C@H:24]([C@H:25]4[C@H:35]([CH2:36][CH2:37]3)[C@:33]3([CH3:34])[C:28](=[CH:29][C:30](=[O:41])[C@@H:31]5[O:40][C@@H:32]53)C=C4)[CH2:23][CH2:22]2)C)OC1>C(Cl)(Cl)Cl>[O:40]1[C:31]2=[C:32]3[C@:33]([CH3:34])([CH2:28][CH2:29][C:30]2=[O:41])[C@@H:35]2[C@H:25]([C@H:24]4[C@:38]([CH3:39])([CH2:37][CH2:36]2)[C@@H:21]([CH2:19][CH3:16])[CH2:22][CH2:23]4)[C@@H:4]2[O:10][C@:8]123

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

Product 1

HCID 867457986alpha,7alpha-Diepoxypregn-4-en-3oneYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 0.664 g (3.85 mmoles) of m-chloroperbenzoic acid in 50 ml of chloroform was mixed with a solution of 0.328 g (0.769 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one in 10 ml of chloroform and the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was filtered and the precipitate was washed with chloroform. The filtrate and the washings were combined, diluted with chloroform and washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution. Finally the organic layer was dried over magnesium sulfate and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane: 1:10, v/v) to recover 0.258 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3-one (yield: 76%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with chloroform
  3. additiondiluted with chloroform
  4. washwashed successively with aqueous potassium iodide solution and aqueous sodium chloride solution
  5. dry with materialFinally the 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
  8. customethyl acetate-hexane: 1:10, v/v) to recover 0.258 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α

Sources & evidence

ORD record
ord-a6b67676d46f4cfcadc27ac7261c0425
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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