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

HRID 7411

反応式

HRID 7411 の反応式
[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

参加物

5

反応物 2

HCID 9904NandroloneHCID 77620884Tricaprylylmethyl ammonium chloride

生成物 1

HCID 2163421217beta-Hydroxy-5beta-estran-3-one収率 107%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-825838bf0675463188070eeb1a8507bd
出典データセット
uspto-grants-2006_08
特許番号
US07087590B2

関連ノート

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