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

HRID 2117155Notes

Reaction equation

HRID 2117155 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-6935b56d2d79410c85ebb986dc3894c3
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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