Water → tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Participants

Reaction Steps

To a stirred solution of ethyl 6-(bis(tert-butoxycarbonyl)amino)nicotinate 115 (300 g, 819 mmol) in THF (1.2 L) was added LiAlH4 (57.6 g, 1.51 mol) in THF (3 L) over a period of 30 min at 0° C. The reaction mixture was stirred for 6 h, and H2O (30.0 ml) and 10% NaOH solution (60.0 mL) were added. The solids were removed by filtration and the filtrate was dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (CH2Cl2; MeOH=40:1) to give 116 (85.0 g, 46% yield).

Provenance & Evidence