Cortisol → 11beta-Hydroxyandrost-4-ene-3,17-dione

HRID 80415

Reaktionsgleichung

Reaktionsgleichung von HRID 80415
[CH3:1][C@@:2]12[C@H:12]3[C@@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])(C(CO)=O)[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[O-][Bi](=O)=O.[Na+]>C(O)(=O)C>[OH:26][C@H:13]1[CH2:14][C@@:15]2([CH3:25])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:24])[C@H:11]2[C@H:12]1[C@:2]1([CH3:1])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 5754CortisolHCID 4063671Sodium bismuthate

Produkt 1

HCID 9414111beta-Hydroxyandrost-4-ene-3,17-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. washwashed with dichloromethane
  3. customThe organic phase was separated
  4. washwashed with water and neutralised with sodium bicarbonate (to pH 8)
  5. customThe organic phase was again separated
  6. washwashed
  7. customdried
  8. filtrationfiltered
  9. customFinally, the organic solvent was removed under reduced pressure
  10. customby recrystallising from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-c893b0bf3df64b33afa12daa136006fc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846652B2

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