Sodium Bicarbonate → tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Participants

Reaction Steps

A mixture of (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (as the methyl hemiacetal) (1.09 g, 5.291 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (1.06 g, 5.291 mmol) in chloroform (50 ml) and MeOH (2.5 ml) was stirred for 2 h before addition of NaBH(OAc)3 (3.37 g, 15.873 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the desired compound (1.591 g, 77%).

Provenance & Evidence