Reaktion #354820

ord-ff1601e1bbdb440faa7fdc546d11b121

Reaktionsgleichung

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C#N)[C@@]3(C)CC(=O)[C@@H]12
17β-cyano-5α-androst-2-en-11-one
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
→
C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C#N)[C@@]3(C)CC(=O)[C@@H]12
title compound
C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C#N)[C@@]3(C)CC(=O)[C@@H]12
17β-Cyano-2α,3α-epoxy-5α-androstan-11-one

Edukte

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C#N)[C@@]3(C)CC(=O)[C@@H]12
17β-cyano-5α-androst-2-en-11-one
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform
ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThis solution was washed with aqueous 10% sodium bicarbonate and water
  2. 2
    Sonstigeto drying
  3. 3
    FiltrationFiltration and evaporation
  4. 4
    Sonstigeafforded a solid (3.18g.) which
  5. 5
    Sonstigewas recrystallised from ether/petrol

Vorschrift

A solution of 17β-cyano-5α-androst-2-en-11-one (2.8g.) and 85% m-chloroperbenzoic acid (2.0g.) in chloroform (50 ml.) was stirred for 1.5 hour at room temperature and then diluted with chloroform (75 ml.). This solution was washed with aqueous 10% sodium bicarbonate and water prior to drying. Filtration and evaporation afforded a solid (3.18g.) which was recrystallised from ether/petrol to afford the pure title compound; m.p. 206°-208°; [α]D + 93°, (c 0.7).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03943124uspto-grants-1976_03