Nandrolone → (+)-Estr-4-ene-3,17-dione

HRID 651369

Reaction equation

HRID 651369 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

HCID 9904Nandrolone

Product 1

HCID 92834(+)-Estr-4-ene-3,17-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to half of its initial volume
  2. additionpoured into 1 M hydrochloric acid (500 mL)
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aqueous NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7cbba40be0b4b2e95412a85e47d369f
Source dataset
uspto-grants-2001_08
Patent number
US06281205B1

Linked notes

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