反应详情

Lithium diisopropylamide (from n-butyllithium, 1.55M in hexane; (57.3 ml) and diisopropylamine (11.64 ml) in THF (45 ml) was added dropwise over 15 min. at -5° under nitrogen to a stirred suspension of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (15 g) in THF (510 ml). After 45 min., Intermediate 2 (26.5 g) was added in one portion and the resultant solution was stirred at -5° to +5° for 1.75 h. The solution was treated with acetic acid at below 20° and stirred for 1 h. Methanesulphonic acid (34 ml) was added and the mixture was stirred and heated under reflux for 16 h. The resultant suspension was cooled to 5°, stirred at below 5° for 1 h and the solid was filtered off. The product was washed with THF (2×50 ml) and dried in vacuo at 50° to give a solid (28.5 g) which was recrystallised from methanol to give the title compound (17 g), m.p. 264.5°-267°.

1. stirringthe mixture was stirred
2. temperatureheated
3. temperatureunder reflux for 16 h
4. stirringstirred at below 5° for 1 h
5. filtrationthe solid was filtered off
6. washThe product was washed with THF (2×50 ml)
7. customdried in vacuo at 50°