Aluminium lithium hydride → tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)nicotinate (100; 10.0 g, 27.3 mmol) in THF (40 mL) was added LiAlH4 (1.92 g, 50.5 mmol) in THF (60 mL) over a period of 30 min at 0° C. The resulting reaction mixture was stirred at 0° C. for 6 h. The reaction was then quenched by carefully adding water (1.0 ml) and 10% NaOH solution (2.0 mL) at 0° C. The resulting mixture was filtered and the filtrate was dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (dichloromethane:methanol=40:1) to afford tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate 101 (4.50 g, 74%).

Provenance & Evidence