[F:1][C:2]1[C:7]([CH:8]([CH2:14][N+:15]([O-])=O)[CH2:9][C:10](OC)=[O:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CCO.[Ni](Cl)Cl>[F:1][C:2]1[C:7]([CH:8]2[CH2:14][NH:15][C:10](=[O:11])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1To a solution of methyl 3-(2-fluoropyridin-3-yl)-4-nitrobutanoate (0.991 g, 4.09 mmol) in EtOH (20 mL) at 0° C. was added nickel chloride (0.532 g, 4.10 mmol) and sodium borohydride (1.60 g, 42.3 mmol). The reaction mixture was stirred at 0° C. for 30 min, warmed to room temperature over 30 min, and stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous KH2PO4 and diluted with water and EtOAc. The mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc (6×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 10% MeOH in DCM) gave 4-(2-fluoropyridin-3-yl)pyrrolidin-2-one (0.168 g, 0.932 mmol, 23% yield) as a colorless oil. MS (ESI, pos. ion) m/z: 181.1 (M+1).
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