[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.CO.C([O-])(=O)C.[Na+].Cl.[NH2:22][OH:23]>CC(OC)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=[N:22][OH:23])[CH2:9]2)=[CH:4][CH:3]=1
A slurry of (S)-3-(4-bromophenyl)cyclopentanone (prepared according to J. Org. Chem., 2009, 74, 929; 10.9 g, 45.5 mmol), MeOH (110 mL), sodium acetate (5.59 g, 68.2 mmol), and hydroxylamine hydrochloride (4.74 g, 68.2 mmol) was stirred at room temperature. After 10 minutes, LCMS showed complete reaction. Diluted with MTBE (300 mL) and washed with water (100 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (gradient elution, 25-50% EtOAc/hexanes) to afford the title compound (11.0 g, 43.3 mmol, 95%). MS (DCI) m/z 254 (M+H)+.
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