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

HRID 889062
Notes
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Reaction equation

HRID 889062 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

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

  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

Sources & evidence

ORD record
ord-1e19da1f52ab4b94aaf7b10ef67ab7ff
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08252797B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes