Triethylamine → Phenylmethyl [((3S)-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) 1:4 (MeOH/CH2Cl2) (40 mL) were added phenylmethyl [(3R)-3-pyrrolidinyl-methyl]carbamate (for a synthesis see WO2006002047 Preparation 23(b)) (0.536 g, 2.29 mmol) and triethylamine (0.351 mL, 2.52 mmol) and the resulting solution stirred at ambient temperature for 1 h. Na(OAc)3BH (1.46 g, 6.87 mmol) was added and the solution stirred an additional 18 hours. 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, (0.333 g, 33%).

Provenance & Evidence