Triethylamine → HCID 59899161, compound

Participants

Reaction Steps

To a stirred suspension of 5-5 (170 mg, 0.44 mmol), triethylamine (61 mL, 0.44 mmol), and 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbaldehyde (72 mg, 0.44 mmol) in 1,2-dichloroethane (4 mL) was added sodium triacetoxyborohydride (112 mg, 0.53 mmol) and the resulting mixture was stirred for 1.5 hours. The reaction mixture poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was then washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Following evaporative removal of the solvent, the residue was purified by flash column chromatography (silica gel, 95:5:0.5:0.5% ethyl acetate/ethanol/NH4OH/H2O) to give 5-6 as a colorless oil.

Provenance & Evidence