Hydrochloric Acid → (3aS,12bS)-5-Chloro-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole

Participants

Reaction Steps

1.55 g (5.4 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) was dissolved in 32.5 mL of anhydrous tetrahydrofuran. 2.1 mL of N,N-diethylaniline-borane complex (11.5 mmol) were added dropwise and the obtained solution was stirred at room temperature for 30 min before heating to reflux. The reaction mixture was stirred for 8 h then it was allowed to cool to room temperature overnight. The mixture was reheated to reflux and stirred for 5 h before allowing to cool down to room temperature. 3 mL of a 6 M hydrochloric acid were added and the mixture refluxed for 1 h and overnight at room temperature. The mixture was then basified with 95 mL of 0.25 M potassium hydroxide and extracted with diethyl ether (50 mL), three times. The organic layers were combined and dried with anhydrous sodium sulfate, filtered and rotary evaporated.

Provenance & Evidence