反应详情

温度

-78 °C

A solution of 2-tert-butoxycarbonylamino-4-methylpyridine (146 g, 0.700 mol) in anhydrous tetrahydrofuran (1.30 L) was cooled to −78° C. and, with stirring, a solution of 1.6 M n-butyl lithium in hexane (875 mL, 1.40 mol) was added dropwise. After the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. and cooled to −78° C. A solution of N-(3-methylbenzoyl)propyleneimine (123 g, 0.700 mol) in anhydrous tetrahydrofuran (130 mL) was added dropwise. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr., warmed to room temperature and stirred for 1 hr. Saturated brine (1.30 L) was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried and concentrated. The crude crystals were recrystallized from ethyl acetate to give the title compound (185 g, yield 81%).

1. additionAfter the completion of the dropwise addition
2. stirringthe mixture was stirred at 0° C. for 30 min.
3. additionAfter the completion of the dropwise addition
4. stirringthe mixture was stirred at −78° C. for 1 hr
5. temperature, warmed to room temperature
6. stirringstirred for 1 hr
7. customthe organic layer was separated
8. extractionThe aqueous layer was extracted with ethyl acetate
9. customthe combined organic layer was dried
10. concentrationconcentrated
11. customThe crude crystals were recrystallized from ethyl acetate