Nandrolone → 17beta-Hydroxy-5beta-estran-3-one

HRID 7411

Reaction equation

HRID 7411 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.CCCCCCCC(C([NH3+])(C(CCCCCCC)=O)C(CCCCCCC)=O)=O.[Cl-]>ClCCl.O>[OH:11][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:5]([CH2:4][CH2:3][C@:2]12[CH3:1])[C@@H:20]1[C@@H:14]([CH2:15][C:16](=[O:17])[CH2:18][CH2:19]1)[CH2:13][CH2:12]3

Participants

5

Reactant 2

HCID 9904NandroloneHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 2163421217beta-Hydroxy-5beta-estran-3-oneYield 107%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 19-nortestosterone (10.0 g, 35.5 mmol) in dichloromethane (100.0 ml) was mixed with the catalyst previously prepared from RhCl3.H2O (380 mg) and Aliquat-336® (800 mg) in water (10.0 ml) and dichloromethane (22.0 ml). The mixture was hydrogenated overnight at 20 psi. The product was washed twice with water (40 ml) and dried on Na2SO4. The catalyst was removed by flash-chromatography on silica gel with CH2Cl2 as eluant to give 10.5 g (92% yield) the title compound as a white solid.

Workup

  1. washThe product was washed twice with water (40 ml)
  2. customdried on Na2SO4
  3. customThe catalyst was removed by flash-chromatography on silica gel with CH2Cl2 as eluant

Sources & evidence

ORD record
ord-825838bf0675463188070eeb1a8507bd
Source dataset
uspto-grants-2006_08
Patent number
US07087590B2

Linked notes

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