Réaction #167597

ord-c893b0bf3df64b33afa12daa136006fc

Équation de réaction

[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

Réactifs

[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

Réactifs

Aucun

Solvants

CC(=O)O
acetic acid

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08846652B2uspto-grants-2014_09