4-Toluenesulfonyl chloride → trans-(-)-Octahydro-7-[[[(4-methylphenyl)sulfonyl]oxy]methylene]-1-(n-propyl)-6(2H)-quinolinone

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence