HCID 57988768, compound → 4-Acetyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one

HRID 889045Notes

Reaction equation

HRID 889045 reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH2:7]1)=[O:5].[CH3:23][Mg]Br>C1COCC1>[C:4]([CH:6]1[CH2:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[C:9](=[O:11])[CH2:10]1)(=[O:5])[CH3:23]

Participants

4

Reactant 2

HCID 57988768HCID 57988768, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 574296654-Acetyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (0.6 g, 1.89 mmol) in THF (6 mL) was added methylmagnesium bromide (1.6 ml, 4.74 mmol, 3.0M in ether) drop wise over a period of 10 min at 0° C. The reaction mixture was stirred for 3 h at room temperature. The reaction mixture was quenched with saturated ammonium chloride solution (2 ml) and extracted with ethyl acetate (2×15 ml). The combined organic layer was washed with saturated brine solution (25 ml). The organic layer was dried over Na2SO4, evaporated to obtain 4-Acetyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one as a brown oil (0.5 g, 97%).

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (2 ml)
  2. extractionextracted with ethyl acetate (2×15 ml)
  3. washThe combined organic layer was washed with saturated brine solution (25 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ddfe1a7e4c2f4135b97b88ac1fdc39f3
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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