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

Temperature

-2 °C

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.

1. addition8.8 mL of borane-tetrahydrofuran complex (8.7 mmol) were added dropwise
2. temperatureto warm up to room temperature
3. waitAfter further 25 h at room temperature
4. addition8.8 mL of borane-tetrahydrofuran complex (8.7 mmol) were added
5. stirringthe mixture stirred for 4 h
6. customAfter 3 days the reaction mixture was rotary evaporated
7. additiontoluene (25 mL) and 1 M sodium hydroxide (10.5 mL) were added to the residue
8. additionMore toluene (25 mL) and water (10 mL) were added
9. stirringthe mixture vigorously stirred for about 2.5 h
10. customThen the layers were separated
11. extractionthe aqueous layer was extracted with toluene (25 mL)
12. washwashed with 0.1 M sodium hydroxide (4 mL)
13. dry with materialdried with anhydrous sodium sulfate
14. filtrationfiltered

ORD record

ord-fe93bcc73ba24678965b5ec6ad9a40f8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580972B2