m-Chloroperbenzoic acid → 2alpha,3alpha-Epoxy-5alpha-pregnan-20-one

HRID 2253805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2253805
[CH3:1][C:2](=[O:22])[C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11][CH:12]=[CH:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[O:31]1[C@H:12]2[CH2:11][C@H:10]3[C@:15]([CH3:16])([CH2:14][C@@H:13]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@:20]([CH3:21])([CH2:19][CH2:18]1)[C@@H:3]([C:2](=[O:22])[CH3:1])[CH2:4][CH2:5]2)[CH2:8][CH2:9]3

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 2468835alpha-Pregn-2-en-20-one

Produkt 1

HCID 543466312alpha,3alpha-Epoxy-5alpha-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

5α-pregnan-2-ene-20-one (3.05 g) in 50 mL of chloroform was treated with m-chloroperbenzoic acid (50-60%, 4.0 g). The solution was stirred at room temperature overnight (14 h) under an argon atmosphere. The solution was diluted with more chloroform (250 mL), washed with dilute potassium bicarbonate solution (2×150 mL), with water (2×100 mL), and finally with brine, and dried over magnesium sulfate and evaporated to an oil which crystallized on standing. Flash chromatography on a silica gel bed (200 g) and eluting with hexane/ethyl acetate (90:10) recovered in fraction 67-110 (collecting 20 mL volumes) 1.194 g of the titled compound.

Aufarbeitung

  1. washwashed with dilute potassium bicarbonate solution (2×150 mL), with water (2×100 mL)
  2. dry with materialfinally with brine, and dried over magnesium sulfate
  3. customevaporated to an oil which
  4. customcrystallized
  5. washFlash chromatography on a silica gel bed (200 g) and eluting with hexane/ethyl acetate (90:10)
  6. customrecovered in fraction 67-110 (collecting 20 mL volumes) 1.194 g of the titled compound

Quellen und Nachweise

ORD-Eintrag
ord-99dd62693fca4ea0ae5723630ce7d2a0
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05232917

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