反应详情

温度

0 °C

To a mixture of 1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid (synthesized according to the method described in Bioorg. Med. Chem., 8, 5, 2000, 1041-1058, 3.9 g), triethylamine (2.87 ml) and benzene (12 ml) was added diphenylphosphoryl azide (Aldrich Co., 4.44 ml) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was passed through a silica gel filter, and the filtrate was evaporated under reduced pressure to give a pale-yellow oil. Toluene (20 ml) was added to the oil, and the mixture was heated under reflux for 2 hr. The solvent was evaporated under reduced pressure. Dichloromethane (35 ml) and lead tetracetate (5.70 g) were added to the obtained residue. Thereafter, 1-aminobenzotriazole (Aldrich Co., 1.54 g) was dissolved in dichloromethane (15 ml) was added thereto. The mixture was stirred at room temperature for 30 min. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 6-oxo-1,4,5,6-tetrahydrobenzo[c]-1,7-naphthyridine-3(2H)-carboxylic acid tert-butyl ester (1.14 g, yield 33%).

1. customsynthesized
2. temperaturecooling
3. filtrationfilter
4. customthe filtrate was evaporated under reduced pressure
5. customto give a pale-yellow oil
6. temperaturethe mixture was heated
7. temperatureunder reflux for 2 hr
8. customThe solvent was evaporated under reduced pressure
9. additionDichloromethane (35 ml) and lead tetracetate (5.70 g) were added to the obtained residue
10. dissolutionThereafter, 1-aminobenzotriazole (Aldrich Co., 1.54 g) was dissolved in dichloromethane (15 ml)
11. additionwas added
12. stirringThe mixture was stirred at room temperature for 30 min
13. filtrationThe reaction mixture was filtered
14. customthe filtrate was evaporated under reduced pressure
15. customThe obtained residue was purified by silica gel column chromatography