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

HRID 1196315ノート

反応式

HRID 1196315 の反応式
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[C@@H:20]5[O:29][C@@H:21]53)C=C4)[CH2:12][CH2:11]2)C)OC1.C(=O)([O-])O.[Na+].ClC1C=CC=[C:40]([C:44]([O:46]O)=O)C=1>C(Cl)Cl>[O:29]1[C:20]2=[C:21]3[C@:22]([CH3:23])([CH2:17][CH2:18][C:19]2=[O:30])[C@@H:24]2[C@H:14]([C@H:13]4[C@:27]([CH3:28])([CH2:26][CH2:25]2)[C@@H:10]([CH2:8][CH3:5])[CH2:11][CH2:12]4)[C@@H:40]2[O:46][C@:44]123

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

生成物 1

HCID 867457986alpha,7alpha-Diepoxypregn-4-en-3one収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.43 g (1.0 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one in 10 ml of methylene chloride was added 3 ml of 0.5M-aqueous sodium hydrogen carbonate solution under stirring and cooling in an ice-water bath, followed by gradual addition of 0.34 g (2.0 mmoles) of m-chloroperbenzoic acid. The mixture was stirred at room temperature for 2 days. The reaction mixture thus obtained was subjected to phase separation and the aqueous layer was extracted twice with 10 ml portions of methylene chloride. The extract was combined with the organic layer obtained above and the mixture was washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution, and 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 0.35 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3-one (yield: 79%). The 1H-MNR and IR spectra of this product were in agreement with those of the 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3-one obtained in Example 7.

後処理

  1. temperaturecooling in an ice-water bath
  2. stirringThe mixture was stirred at room temperature for 2 days
  3. customThe reaction mixture thus obtained
  4. customwas subjected to phase separation
  5. extractionthe aqueous layer was extracted twice with 10 ml portions of methylene chloride
  6. customobtained above and the mixture
  7. washwas washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure
  10. customthe residue was purified by silica gel chromatography (eluent
  11. customethyl acetate-hexane=1:10, v/v) to recover 0.35 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α

出典と根拠

ORDレコード
ord-04fbe2cbf15341f9878aad9f4219b31f
出典データセット
uspto-grants-1992_05
特許番号
US05112998

反応ノート

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