Acetone → 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester
Reaction equation
[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]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
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%).
Workup
- filtrationThe reaction mixture was filtered
- customevaporated
- extractionextracted with DCM (100×3 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated on a rotary evaporator
- customto afford the crude product mixture
Sources & evidence
- ORD record
- ord-1e19da1f52ab4b94aaf7b10ef67ab7ff
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252797B2
Reaction notes
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