Reaktion #354812

ord-adfd62dbdd12400fb3ddd3395d3ba9e0

Reaktionsgleichung

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)c5ccc(C)cc5)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-methoxycarbonyl-3β-toluene-p-sulphonyloxy-5α-androstan-11-one
Cl
hydrochloric acid
→
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
title compound
Ausbeute 51.2%
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-Methoxycarbonyl-5α-androstan-2-en-11-one
Ausbeute 51.2%

Edukte

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)c5ccc(C)cc5)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-methoxycarbonyl-3β-toluene-p-sulphonyloxy-5α-androstan-11-one
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

Cc1cc(C)nc(C)c1
collidine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe solution was cooled
  2. 2
    FiltrationThe product was filtered
  3. 3
    Waschenwashed with water
  4. 4
    Sonstigedried
  5. 5
    Sonstigepurified
  6. 6
    Filtrationby filtering it through a column of alumina
  7. 7
    Wascheneluting with ether
  8. 8
    SonstigeThe eluate was evaporated to a residue and crystallisation from ether and hexane

Vorschrift

A solution of 17β-methoxycarbonyl-3β-toluene-p-sulphonyloxy-5α-androstan-11-one (1.01g.) in hot collidine (5 ml.) was refluxed for 30 minutes. The solution was cooled and poured into diluted hydrochloric acid and ice, and stirred. The product was filtered, washed with water, dried and purified by filtering it through a column of alumina, eluting with ether. The eluate was evaporated to a residue and crystallisation from ether and hexane gave title compound (340 mg.) as colourless rods; m.p. 169°-175°; [α]D + 139°.

Quelle

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