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

HRID 889062
ノート
印刷プレビュー

反応式

HRID 889062 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1e19da1f52ab4b94aaf7b10ef67ab7ff
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08252797B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート