[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:14])=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:7]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:14])=[C:6]([N:8]3[CH2:12][CH2:11][CH2:10][C:9]3=[O:13])[CH:7]=2)=[CH:18][CH:17]=1A solution of 1-(5-amino-2-fluoro-phenyl)-pyrrolidin-2-one (0.34 g, 1.8 mmol), 4-chlorobenzaldehyde (0.25 g, 1.8 mmol) and sodium triacetoxyborohydride (0.75 g 3.6 mmol) was stirred in dry dichloromethane (25 ml) overnight. The reaction was quenched with water (25 ml) and the dichloromethane layer separated, dried (magnesium sulphate) and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2) eluting with ethyl acetate/dichloromethane (1:10) to afford the title compound as a yellow oil (253 mg, 44%). HPLC retention time 4.4 min, Mass spectrum (ES+) m/z 319 (M+H).
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