Sodium Sulfate → 1,1-Dimethylethyl [((2S)-4-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-2-morpholinyl)methyl]carbamate

Participants

Reaction Steps

To a solution of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (0.500 g, 2.29 mmol) in 1:1 (MeOH/CHCl3) (25 mL) were added 1,1-dimethylethyl [(2R)-2-morpholinyl-methyl]carbamate (0.500 g, 2.29 mmol) and Na2SO4 (0.100 g) and the resulting solution stirred at ambient temperature for 18 h. Na(OAc)3BH (1.46 g, 6.87 mmol) was added and the solution stirred an additional 2 g. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column) [0-100% Hexanes/EtOAc] to yield a yellowish oil. (0.460 g, 48%)

Provenance & Evidence