General procedure for the synthesis of 4-(hydroxymethyl)pyridin-2(1H)-one from methyl 2-hydroxypyridine-4-carboxylate: to an anhydrous tetrahydrofuran (23 mL) suspension of methyl 2-methoxy-1,2-dihydro-4-pyridinecarboxylate (1.37 g, 8.98 mmol) was added slowly and dropwise 2 M lithium borohydride/tetrahydrofuran solution (22.5 mL, 45 mmol). The reaction mixture was heated to 55 °C and maintained for 3.5 h under nitrogen protection. Upon completion of the reaction, methanol (15 mL) and water (3 mL) were carefully added, followed by stirring for 30 min at room temperature. The mixture was concentrated and methanol (10 mL) was again carefully added. After continued stirring for 30 min, the mixture was adsorbed onto silica gel and purified by silica gel column chromatography using a 0 to 30% methanol-dichloromethane gradient elution to afford the target product, 4-(hydroxymethyl)pyridin-2(1H)-one, as an off-white solid (0.99 g, 88% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 11.29 (br s, 1H), 7.23 (d, J = 6.7 Hz, 1H), 6.21 (s, 1H), 6.03 (dd, J = 6.7, 1.3 Hz, 1H), 5.27 (t, J = 5.9 Hz, 1H), 4.28 (d, J = 5.9 Hz, 2H).
