Nandrolone → (+)-Estr-4-ene-3,17-dione
Reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3>C(O)(=O)C>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:12][CH2:13][C:14]4[C@@H:20]3[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=4)[C@@H:7]1[CH2:8][CH2:9][C:10]2=[O:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 19-nortestosterone 52 (26.85 g, 97.85 mmol) in acetic acid (200 mL) was added a CrO3 (7.4 g, 74 mmol) in acetic acid (150 mL) and stirred for 1 h at room temperature. The reaction mixture was concentrated under reduced pressure to half of its initial volume, poured into 1 M hydrochloric acid (500 mL) and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and then concentrated to afford dione 53 as a white solid (25.3 g, 95%): 1H NMR (300 MHz, CDCl3) δ0.94 (s, 3, CH3), 5.85 (s, 1).