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

HRID 80415

Reaction equation

HRID 80415 reaction equation
[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

Participants

4

Reactant 2

HCID 5754CortisolHCID 4063671Sodium bismuthate

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c893b0bf3df64b33afa12daa136006fc
Source dataset
uspto-grants-2014_09
Patent number
US08846652B2

Linked notes

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