p-Fluoronitrobenzene → (R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

HRID 1441370Notes

Reaction equation

HRID 1441370 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][N:18]([CH3:26])[C:19]([C@H:21]1[CH2:25][CH2:24][CH2:23][NH:22]1)=[O:20]>C(#N)C>[CH3:17][N:18]([CH3:26])[C:19]([C@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 7021808(2R)-N,N-dimethylpyrrolidine-2-carboxamide

Product 1

HCID 68687436(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Fluoronitrobenzene (0.47 g, 3.34 mmol), potassium carbonate (1.39, 10 mmol) and (R)-pyrrolidine-2-carboxylic acid dimethylamide (0.50, 3.52 mmol) were pre-mixed in acetonitrile (40 ml) and heated at reflux for 36 hours. The reaction was quenched with saturated ammonium chloride (40 ml), extracted with DCM (2×100 ml), dried and solvent removed in vacuo to yield the title compound as a yellow solid. Ether was added and the solid was stirred, filtered and dried (0.85 g, 96%). M/z 264.

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. customThe reaction was quenched with saturated ammonium chloride (40 ml)
  4. extractionextracted with DCM (2×100 ml)
  5. customdried
  6. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-897a644ce1c642e4b2cd23122dc0d26e
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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