Reaktion #1693673

ord-434086f0b34a4d4c8b58f756d3cb00ea

Reaktionsgleichung

CC1([C@H]2CC[C@H]3[C@@H]4CC[C@H]5C[C@H](O)CC[C@]5(C)[C@H]4C(=O)C[C@]23C)OCCO1
20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one
CC(=O)O
acetic acid
CC(=O)O
acetic acid
→
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@H](O)C[C@]12C
title compound
Ausbeute 51.5%
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@H](O)C[C@]12C
3α,11α-Dihydroxy-5α-pregnan-20-one
Ausbeute 51.5%

Edukte

CC1([C@H]2CC[C@H]3[C@@H]4CC[C@H]5C[C@H](O)CC[C@]5(C)[C@H]4C(=O)C[C@]23C)OCCO1
20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one
CC(=O)O
acetic acid
CC(=O)O
acetic acid

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with water
  2. 2
    Trocknendried (Na2SO4)
  3. 3
    Sonstigeevaporated
  4. 4
    Sonstigeto leave a white foam (300 mg.)
  5. 5
    SonstigeCrystallisation from acetone and petroleum ether (b.p. 60°-80°)

Vorschrift

A solution of 20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one (350 mg.) in mthanol (20 ml.) was treated with 25% aqueous acetic acid (2 ml.) at room temperature. After 18 hr. more 25 % aqueous acetic acid (2 ml.) was added and after a further 27 hr. the mixture was diluted with chloroform, washed with water, dried (Na2SO4) and evaporated to leave a white foam (300 mg.). Crystallisation from acetone and petroleum ether (b.p. 60°-80°) gave the title compound (160 mg.) as off-white rods; m.p. 152°-154°; [α]D + 79°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03953429uspto-grants-1976_04