Aluminium lithium hydride → tert-butyl N-[6-(hydroxymethyl)pyridin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (112; 8.9 g, 24.0 mmol) in ethyl ether (200 mL) was added LiAlH4 (1.80 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0° C. The resulting reaction mixture was stirred at 0° C. for 3 h and then carefully quenched by carefully adding water (1.0 mL) and 10% NaOH solution (2.0 mL). The mixture was filtered; the filtrate was dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate 113 (4.20 g, 78%).

Provenance & Evidence