Reaktion #93695

ord-91d96e7f9f5f4930bc6681db0aea5d9e

Reaktionsgleichung

C[C@]12CC[C@H](O[Si](Cc3ccccc3)(Cc3ccccc3)Cc3ccccc3)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one
CC(C)(C)OO
tert.-butyl hydroperoxide
→
C[C@]12CC[C@H]3[C@@H]([C@@H](O)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one

Edukte

C[C@]12CC[C@H](O[Si](Cc3ccccc3)(Cc3ccccc3)Cc3ccccc3)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one
—
vanadium(IV) oxide acetylacetonate
CC(C)(C)OO
tert.-butyl hydroperoxide

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling
  2. 2
    Waschenthe mixture is washed with water and saturated sodium chloride solution
  3. 3
    Sonstigedried
  4. 4
    Sonstigeevaporated under vacuum

Vorschrift

24 g of 3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one is dissolved in 50 ml of toluene, combined with 500 mg of vanadium(IV) oxide acetylacetonate, and heated to 80° C. A solution of 75 ml tert.-butyl hydroperoxide (10 ml 80% tert.-butyl hydroperoxide in 100 ml of toluene) is added dropwise to the reaction mixture, and the latter is allowed to stand for 1.5 hours at this temperature. After cooling, the mixture is washed with water and saturated sodium chloride solution, dried, and evaporated under vacuum, thus obtaining 24.5 g of 3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04614616uspto-grants-1986_09