Hydrochloric Acid → HCID 67979894, compound

Temperature

0 °C

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.

1. customequipped with a Dean-Stark distillation setup
2. temperatureThe mixture was heated
3. temperatureto reflux
4. stirringthe mixture stirred for about 30 minutes
5. temperatureto heat to room temperature
6. stirringstirred over about 20 h
7. temperaturethe mixture heated
8. temperatureto reflux
9. stirringstirred for 2 h
10. temperatureto cool down to room temperature
11. customthe obtained layers were separated
12. extractionThe aqueous layer was extracted with diethyl ether (26 mL) three times
13. dry with materialthe obtained organic layers were dried with sodium sulfate
14. filtrationfiltered
15. customrotary evaporated
16. customdried in the vacuum oven

ORD record

ord-96d0c4bd93d047e6a910b3ec32064ce5

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580972B2