[BH4-].[Na+].[Br:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][C:12](=[O:17])[CH2:13]3)=[CH:6][CH:5]=1>CO.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][CH:12]([OH:17])[CH2:13]3)=[CH:18][CH:19]=1Sodium borohydride (95 mg, 1.50 mmol) was added to a solution of 8-(4-bromobenzyl)-8-azabicyclo-[3.2.1]octan-3-one (0.22 g, 0.75 mmol) in methanol (10 mL) and the reaction mixture was stirred for 30 minutes. The reaction was diluted with water (10 mL) and extracted into DCM (3×20 mL). The combined organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as an off-white solid (200 mg, 90%). 1H NMR (CDCl3, 300 MHz): 7.43 (dd, J=8.3, 2.0 Hz, 3H), 7.29-7.23 (m, 2H), 3.60-3.45 (m, 2H), 3.23-3.10 (m, 2H), 2.16-1.40 (m, 8H). LCMS (Method B): RT=1.90 min, M+H+=296/298.
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