Reaktion #354803

ord-1649bf722b3c427887c307b0423678c0

Reaktionsgleichung

Br
hydrobromic 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
17β-cyano-2α,3α-epoxy-5α-androstan-11-one
→
C[C@]12C[C@H](Br)[C@@H](O)C[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](Br)[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C#N)[C@@]3(C)CC(=O)[C@@H]12
2β-Bromo-17β-cyano-3α-hydroxy-5α-androstan-11-one

Edukte

Br
hydrobromic 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
17β-cyano-2α,3α-epoxy-5α-androstan-11-one

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe organic phase was separated
  2. 2
    Waschenwashed with aqueous 10% sodium bicarbonate and water
  3. 3
    Sonstigedried
  4. 4
    FiltrationFiltration and evaporation

Vorschrift

Aqueous 48% hydrobromic acid (60 ml.) was added to a solution of 17β-cyano-2α,3α-epoxy-5α-androstan-11-one (3.03g.) in chloroform (175ml.) and the mixture stirred at room temperature for 1 hr. The organic phase was separated, washed with aqueous 10% sodium bicarbonate and water and dried. Filtration and evaporation followed by preparative t.l.c. afforded the pure title compound as a white froth (2.16g.); [α]D + 68.5°, (c 0.6).

Quelle

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