Triethylamine → HCID 23121852, compound

Participants

Reaction Steps

8-Quinolinecarboxylic acid (0.17 g, 1.0 mmol) was suspended in toluene (5 mL). With ice cooling, triethylamine (0.14 mL, 1.0 mmol) and diphenylphosphoryl azide (0.28 g, 1.0 mmol) were sequentially added thereto, and the mixture was stirred at room temperature for 1 hour and then at 80° C. for 3 hour. After cooling to 50° C., tetrahydrofuran (5 mL) and hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (88 mg, 0.30 mmol) were added thereto, and the mixture was stirred at 50° C. overnight. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate) to obtain the title compound (46 mg, yield 33%).

Provenance & Evidence