Reaktion #354819

ord-038dff8679e547fc81cedbb1e9756d27

Reaktionsgleichung

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(N)=O)[C@@]3(C)CC(=O)[C@@H]12
17β-Carbamoyl-5α-androst-2-en-11-one
→
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
title compound
Ausbeute 56.1%
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
Ausbeute 56.1%

Edukte

—
polyphosphate ester
C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(N)=O)[C@@]3(C)CC(=O)[C@@H]12
17β-Carbamoyl-5α-androst-2-en-11-one

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe chloroform was removed by evaporation
  2. 2
    ExtraktionThe mixture was extracted with ether
  3. 3
    Waschenthe extract washed (H2O)
  4. 4
    Sonstigedried
  5. 5
    Filtrationfiltered
  6. 6
    Sonstigeevaporated
  7. 7
    Sonstigeto give a solid which
  8. 8
    Sonstigeafter recrystallisation from chloroform/cyclohexane

Vorschrift

17β-Carbamoyl-5α-androst-2-en-11-one (4.0g., 13 mmole) and polyphosphate ester (20g.) were refluxed in chloroform (200 ml.) for 20 hr. The chloroform was removed by evaporation and the residue stirred with aqueous 10% sodium carbonate (150 ml.) for an hour. The mixture was extracted with ether and the extract washed (H2O), dried filtered and evaporated to give a solid which, after recrystallisation from chloroform/cyclohexane, gave the title compound (2.17g); m.p. 189°-191°; [α]D + 152°, (c 0.9).

Quelle

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