Water → Atamestane

HRID 275062

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HRID 275062 반응식
I[C@H:2]1[C@H:19]([CH3:20])[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3]1=[O:23].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[CH3:20][C:19]1[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3](=[O:23])[CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 111443782beta-Iodo-1alpha-methylandrost-4-ene-3,17-dione

생성물 1

HCID 57050Atamestane

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.13 g (5 mmol) of 2β-iodo-1α-methylandrost-4-ene-3,17-dione of example 1 is introduced in a suspension of 0.73 g (10 mmol) of lithium carbonate in 10 ml of dimethylformamide preheated to 130° C. and stirred for 1.5 hours at this temperature. After cooling, the reaction solution is added to 30 ml of water, extracted with ethyl acetate and after drying on sodium sulfate, concentrated by evaporation. The crude product is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent. After recrystallization from ethyl acetate, 1.1 g of 1-methylandrosta-1,4-diene-3,17-dione (74% of theory) of melting point 169° C. is obtained.

후처리

  1. custompreheated to 130° C.
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customafter drying on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe crude product is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
  7. customAfter recrystallization from ethyl acetate, 1.1 g of 1-methylandrosta-1,4-diene-3,17-dione (74% of theory) of melting point 169° C.
  8. customis obtained

출처 및 근거

ORD 기록
ord-aa91c1a6b35442468f6d75d761b5b33b
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391778

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