Triethylamine → HCID 59899164, compound

Participants

Reaction Steps

To a stirred suspension of 4-8 (250 mg, 0.57 mmol), triethylamine (80 mL, 0.57 mmol), and 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde (for preparation, see U.S. Pat. No. 6,048,861) (93 mg, 0.57 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (182 mg, 0.86 mmol) and the resulting mixture was stirred for 1.5 hours. The reaction mixture was 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, then 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 4-9 as a colorless oil.

Provenance & Evidence