C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([S:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([C:27]3[NH:32][C:31](=[O:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)=[O:26])=[CH:21][CH:20]=2)[CH2:17][CH2:16]1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH:15]1([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:27]3[NH:32][C:31](=[O:33])[C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[CH2:17][CH2:16]1Sodium triacetoxyborohydride (125 mg) was added to a solution of 6-{[4-(cyclopropylsulfanyl)phenyl]carbonyl}-3-(trifluoromethyl)pyridin-2(1H)-one (110 mg) in chloroform (3 mL), and the mixture was stirred at room temperature overnight. An ammonium chloride solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate only) to give 6-{[4-(cyclopropylsulfanyl)phenyl](hydroxy)methyl}-3-(trifluoromethyl)pyridin-2(1H)-one (40 mg, 36%).
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