Hydrochloric Acid → HCID 67979894, compound

Participants

Reaction Conditions

Reaction Steps

0.526 g (1.84 mmol) of trans-11-chloro-2,3,3a,12b-tetrahydro-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (compound trans-XVIIa) and 17.5 mL of toluene were charged to a 50 mL round-bottomed flask equipped with a Dean-Stark distillation setup. The mixture was heated to reflux and stirred for about 10 min before it was cooled to 0° C. Then trifluoromethanesulfonic anhydride (0.32 mL, 1.9 mmol) was added dropwise and the mixture stirred for about 30 minutes. Sodium borohydride (100 mg, 2.6 mmol) was then added followed by anhydrous tetrahydrofuran (8.6 mL). The obtained solution was allowed to heat to room temperature and stirred over about 20 h. Water (8.6 mL) and 1M hydrochloric acid (0.1 mL) were added, and the mixture heated to reflux, stirred for 2 h and allowed to cool down to room temperature. 6 mL of saturated sodium carbonate solution were added, and the obtained layers were separated. The aqueous layer was extracted with diethyl ether (26 mL) three times, and the obtained organic layers were dried with sodium sulfate, filtered, rotary evaporated and dried in the vacuum oven to yield 0.797 g of a crude oil.

Provenance & Evidence