Cortisol → 11beta-Hydroxyandrost-4-ene-3,17-dione
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.