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

HRID 1196314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196314
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a6b67676d46f4cfcadc27ac7261c0425
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112998

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