[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1
To a mixture of 1-(6-bromopyridin-3-yl)-2-methoxyethanone (15.85 g), tetrahydrofuran (15 mL) and ethanol (15 mL) was slowly added sodium borohydride (0.97 g) at room temperature, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (15.26 g, yield 96%) was obtained as a yellow oil from a fraction eluted with ethyl acetate. MS: 234 (MH+).
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