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

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Reaction Conditions

Reaction Steps

0.53 g (1.9 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 suspended in 5 mL of anhydrous tetrahydrofuran and cooled to −2° C. 8.8 mL of borane-tetrahydrofuran complex (8.7 mmol) were added dropwise and the obtained solution was allowed to warm up to room temperature. The reaction mixture was stirred for 20.5 h and 5 mL of anhydrous tetrahydrofuran were added. After further 25 h at room temperature, 8.8 mL of borane-tetrahydrofuran complex (8.7 mmol) were added and the mixture stirred for 4 h before adding 1.25 M hydrogen chloride in ethanol (25.2 mL, 31.5 mmol). After 3 days the reaction mixture was rotary evaporated and toluene (25 mL) and 1 M sodium hydroxide (10.5 mL) were added to the residue. More toluene (25 mL) and water (10 mL) were added and the mixture vigorously stirred for about 2.5 h. Then the layers were separated and the aqueous layer was extracted with toluene (25 mL), twice. The organic layers were combined and washed with 0.1 M sodium hydroxide (4 mL), dried with anhydrous sodium sulfate, filtered and rotary evaporated.

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