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

Participants

Reaction Steps

A mixture of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (3.807 g, 17.463 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (3.493 g, 17.463 mmol) in chloroform (100 ml) and MeOH (5 ml) was stirred for 1 h before addition of NaBH(OAc)3 (11.11 g, 52.39 mmol). The reaction was stirred for 0.5 h before addition of water (100 ml) and sat. aq NaHCO3 (100 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 0-10% MeOH/DCM gradient to provide the desired compound (5.453 g, 78%).

Provenance & Evidence