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

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.

1. addition2.1 mL of N,N-diethylaniline-borane complex (11.5 mmol) were added dropwise
2. temperaturebefore heating to reflux
3. stirringThe reaction mixture was stirred for 8 h
4. temperatureto cool to room temperature overnight
5. temperatureto reflux
6. stirringstirred for 5 h
7. temperatureto cool down to room temperature
8. temperaturethe mixture refluxed for 1 h and overnight at room temperature
9. extractionextracted with diethyl ether (50 mL), three times
10. dry with materialdried with anhydrous sodium sulfate
11. filtrationfiltered

ORD record

ord-b98856365efb434f8cb0af24062ab5d7

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580972B2