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

HRID 7411

Reaktionsgleichung

Reaktionsgleichung von HRID 7411
[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

Komponenten

5

Edukt 2

HCID 9904NandroloneHCID 77620884Tricaprylylmethyl ammonium chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-825838bf0675463188070eeb1a8507bd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087590B2

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