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

HRID 7411

반응식

HRID 7411 반응식
[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

참가 물질

5

반응물 2

HCID 9904NandroloneHCID 77620884Tricaprylylmethyl ammonium chloride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-825838bf0675463188070eeb1a8507bd
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087590B2

연결된 노트

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