反应详情

温度

0 °C

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)picolinate (92; 11.0 g, 33 mmol) in THF (120 mL) under nitrogen was added LiAlH4 (3.80 g, 100 mmol) in THF (60 mL) over a period of 30 min at 0° C. The reaction mixture was stirred at 0° C. for 6 h and carefully quenched by the addition of water (2.0 mL) and 10% NaOH solution (4.0 mL) at 0° C. The reaction mixture was filtered and the filtrate was dried (Na2SO4) and concentrated under reduced pressure. The resulting residue purified by chromatography (1:1 petroleum ether:ethyl acetate) to afford tert-butyl 6-(hydroxymethyl)pyridin-2-ylcarbamate 93 (3.0 g, 41%).

1. customcarefully quenched by the addition of water (2.0 mL) and 10% NaOH solution (4.0 mL) at 0° C
2. filtrationThe reaction mixture was filtered
3. dry with materialthe filtrate was dried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue purified by chromatography (1:1 petroleum ether:ethyl acetate)