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Acetone → 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 889062
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HRID 889062 반응식
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4](OS(C)(=O)=O)[CH2:3]1.[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[N:29][NH:30][CH:31]=1)=[O:26])[CH3:23].[C:32](=O)([O-])[O-].[K+].[K+].CC(C)=O>CCOC(C)=O.CCCCCC>[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[N:29][N:30]([CH2:32][CH:4]2[CH2:3][C:2](=[O:1])[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=3)[CH2:5]2)[CH:31]=1)=[O:26])[CH3:23]
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7

반응물 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 57429674Methanesulfonic acid 5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl ester

생성물 1

HCID 579887781-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester수율 75.3%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

In an oven dried two-necked round-bottomed flask, the methanesulfonic acid 5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl ester (3.2 g, 9.4 mmol), 1H-pyrazole-4-carboxylic acid ethyl ester (1.46 g, 10.0 mmol), and potassium carbonate (3.93 g, 28.0 mmol) were mixed under an argon atmosphere followed by the addition of the dry acetone (60 mL) at room temperature. The reaction mixture was refluxed at 80° C. for 24 h. The reaction mixture was filtered, evaporated and extracted with DCM (100×3 mL), dried over Na2SO4 and concentrated on a rotary evaporator to afford the crude product mixture. The product was isolated by flash column chromatography (eluting with hexane:EtOAc, 2:3) as a viscous oil (2.7 g, 75%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. extractionextracted with DCM (100×3 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated on a rotary evaporator
  6. customto afford the crude product mixture

출처 및 근거

ORD 기록
ord-1e19da1f52ab4b94aaf7b10ef67ab7ff
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08252797B2

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