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

反応式

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]

参加物

実験手順

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.