Aluminium lithium hydride → Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 6-(bis(tert-butoxycarbonyl)amino)picolinate 77 (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 H2O (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 78 (3.0 g, 41% yield).

Provenance & Evidence