反应详情

温度

-15 °C

A 1 l. 3-neck round bottom flask was purged with nitrogen and charged with 35.0 g (0.312 mol) of potassium t-butoxide. Next, 348 ml of dry tetrahydrofuran was added to the flask and the resulting mixture was cooled to about -15° C. with stirring. To this mixture was added a solution of 30.3 g (0.155 mol) of (8aR-trans)-(-)-octahydro-1-(n-propyl)-6-(2H)-quinolinone in 30 ml of tetrahydrofuran over a period of about 9 minutes while maintaining the temperature of the reaction mixture between about -15° C. and about -17° C. The stirred reaction mixture was allowed to warm to room temperature and the mixture was stirred for 1 hour. The reaction mixture was cooled to about -25° C. and a solution of 23.1 g (25.2 ml, 0.31 mol) of ethyl formate in 45 ml of tetrahydrofuran was added dropwise to the reaction mixture over a period of about 21 minutes. The resulting mixture was stirred for about 30 minutes at about -25° C. and was allowed to warm to about 5° C. The mixture was cooled to about -15° C. and held at that temperature for about 60 hours. The mixture was warmed to about 0° C. and charged with 8.9 ml of glacial acetic acid dropwise. The stirred reaction mixture was cooled to about -37° C. To the mixture was added a solution of 32.6 g (0.171 mol) of p-toluenesulfonyl chloride dissolved in 45 ml of tetrahydrofuran over a period of about 5 minutes. The reaction mixture was warmed to about 0° C. over a period of about 65 minutes and the mixture was held at this temperature for 17.5 hours. The title compound thus prepared was held in situ for further processing.

1. custom3-neck round bottom flask was purged with nitrogen
2. temperaturewhile maintaining the temperature of the reaction mixture between about -15° C. and about -17° C
3. customThe stirred reaction mixture
4. temperatureto warm to room temperature
5. stirringthe mixture was stirred for 1 hour
6. temperatureThe reaction mixture was cooled to about -25° C.
7. stirringThe resulting mixture was stirred for about 30 minutes at about -25° C.
8. temperatureto warm to about 5° C
9. temperatureThe mixture was cooled to about -15° C.
10. temperatureThe mixture was warmed to about 0° C.
11. customThe stirred reaction mixture
12. temperaturewas cooled to about -37° C
13. temperatureThe reaction mixture was warmed to about 0° C. over a period of about 65 minutes
14. waitthe mixture was held at this temperature for 17.5 hours