Triethylamine → phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)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) (40 mL) were added phenylmethyl {[(3S,4R)-4-hydroxypyrrolidin-3-yl]methyl}carbamate (0.658 g, 2.29 mmol) and triethylamine (0.351 mL, 2.52 mmol). The resulting solution was stirred at ambient temperature for 1 h. Na(OAc)3BH (1.46 g, 6.87 mmol) was added and the solution stirred at rt for an additional 18 h. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column [0-100% CHCl3/(90:10:1) CHCl3/MeOH/NH4OH)] to yield a colorless oil (0.760 g, 73%).

Provenance & Evidence