Reaktion #167597

ord-c893b0bf3df64b33afa12daa136006fc

Reaktionsgleichung

[Na+].[O]=[Bi](=[O])[O-]
sodium bismuthate
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone
→
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)C(=O)CC[C@@H]12
11β-Hydroxy-4-androstene-3,17-dione

Edukte

[Na+].[O]=[Bi](=[O])[O-]
sodium bismuthate
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was then filtered
  2. 2
    Waschenwashed with dichloromethane
  3. 3
    SonstigeThe organic phase was separated
  4. 4
    Waschenwashed with water and neutralised with sodium bicarbonate (to pH 8)
  5. 5
    SonstigeThe organic phase was again separated
  6. 6
    Waschenwashed
  7. 7
    Sonstigedried
  8. 8
    Filtrationfiltered
  9. 9
    SonstigeFinally, the organic solvent was removed under reduced pressure
  10. 10
    Sonstigeby recrystallising from ethyl acetate/heptane

Vorschrift

11β-Hydroxy-4-androstene-3,17-dione was synthesised in a single stage, oxidative reaction from hydrocortisone. The starting material was dissolved in acetic acid and allowed to react with sodium bismuthate overnight in the dark. The mixture was then filtered and washed with dichloromethane. The organic phase was separated, washed with water and neutralised with sodium bicarbonate (to pH 8). The organic phase was again separated and then washed, dried and filtered. Finally, the organic solvent was removed under reduced pressure. Pure product was achieved by recrystallising from ethyl acetate/heptane.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846652B2uspto-grants-2014_09