C(O)C.CC(O)C.[Br:8][C:9]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C@H:12]([N+:23]([O-:25])=[O:24])[CH2:11][C:10]=1[CH:26]=[O:27].[BH4-].[Na+].[NH4+].[Cl-]>C(OCC)(=O)C>[Br:8][C:9]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C@H:12]([N+:23]([O-:25])=[O:24])[CH2:11][C:10]=1[CH2:26][OH:27]To a cold (0° C.) ethanol/2-propanol (3 mL/3 mL) solution of Example 7B (758 mg, 2 mmol) under N2 flow, NaBH4 (80 mg, 2.1 mmol) was added. The reaction mixture was stirred and the temperature was allowed to increase from 0° C. to room temperature over two hours. The solution was treated with saturated NH4Cl, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and then purified by flash chromatography with 30% ethyl acetate/hexane to provide the title compound (642 mg, 84%). 1H NMR (300 MHz, CDCl3) δ ppm 7.39-7.51 (m, 1H), 7.26-7.32 (m, 1H), 7.11-7.22 (m, 1H), 5.04-5.20 (m, 1H), 4.31-4.45 (m, 2H), 4.14-4.27 (m, 1H), 2.59-3.32 (m, 4H). MS (DCI) m/z 399 (M+H)+.
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