[CH:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[CH3:18]O>C(OCC)(=O)C>[OH:2][CH:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=1)[CH3:18]To solution of N-(6-formylpyridin-2-yl)-2,2-dimethylpropanamide (3.0 g, 14.9 mmol) in methanol (10 mL) was added sodium borohydride (1.37 g, 37.1 mmol) and stirred for 3 hours. The mixture diluted with ethyl acetate (50 mL). The mixture was washed with aqueous hydrochloric acid (2×30 mL, 0.1 N) and saturated sodium bicarbonate (2×50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford the above-titled intermediate as a white solid (2.49 g, 80%). 1H NMR (400 MHz, CDCl3), δ: 8.16 (d, J=8.3 Hz, 1H), 8.00 (br s, 1H), 7.71 (t, J=7.8 Hz, 1H), 7.12 (d, J=7.5 Hz, 1H), 4.05-3.96 (m, 2H), 1.35 (s, 9H); LRMS (ESI): m/z: 209.2.
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