Sodium borohydride → Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (6-formylpyridin-2-yl)carbamate (13.46 g, 60.57 mmol, 1 eq.) in 200 ml of THF cooled dot 0° C. was added NaBH4 (2.29 g, 60.57 mmol, 1 eq.) portion wise. The reaction was stirred at 0° C. for 1 h and quenched with sat. aqueous NH4Cl. The aqueous layer was extracted with DCM and the organics were combined, dried over MgSO4 and concentrated. The crude residue was purified by chromatography on silica gel to give tert-butyl [6-(hydroxymethyl)pyridin-2-yl]carbamate (9.95 g, 70% yield over 2 steps) as a clear viscous oil.

Provenance & Evidence