tert-Butyl [5-(hydroxymethyl)pyridin-2-yl)carbamate

169280-82-4

169280-83-5

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)nicotinate (100; 10.0 g, 27.3 mmol) in tetrahydrofuran (THF) (40 mL) was slowly added a solution of lithium aluminum hydroxide (LA1H4) (1.92 g, 50.5 mmol) in THF (60 mL) over 30 min, keeping the reaction temperature not below 0 °C. The reaction mixture was continued to be stirred at 0 °C for 6 hours. Upon completion of the reaction, water (1.0 mL) and 10% sodium hydroxide (NaOH) solution (2.0 mL) were carefully added at 0 °C to quench the reaction. The resulting mixture was filtered and the filtrate was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (eluent ratio dichloromethane: methanol = 40:1) to afford the target product tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate 101 (4.50 g, 74% yield).