Water → 1-(4-Fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid

HRID 347550Notes

Reaction equation

HRID 347550 reaction equation
CC1(C)[O:9][C:8](=[O:10])[C:5]2([CH2:7][CH2:6]2)[C:4](=[O:11])O1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.O>CN(C=O)C>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:6][CH2:7][CH:5]([C:8]([OH:9])=[O:10])[C:4]2=[O:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 97314-FluoroanilineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 41820071-(4-Fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6,6-dimethyl-5,7-dioxaspiro[2,5]-octane-4,8-dione (1.02 g, 6.0 mmol, Aldrich) in 3 mL of DMF was added 4-fluorobenzenamine (666 mg, 6.0 mmol, Aldrich). The reaction mixture was stirred at rt overnight. The reaction mixture was poured into cold water (10 mL). The precipitate that formed was collected by filtration, washed with water, and dried under vacuum to afford the desired product (980 mg, 73%) as a tan solid. MS(ESI+) m/z 224.3 (M+H)+.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e928ba1748034be9baf367de6e0a6b71
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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