反应详情

A toluene (10 ml) suspension of (4aS,8aS)-2,2 -dimethyldecahydroquinoxaline (400 mg, 2.38 mmol), 4-bromo-2-chlorobenzonitrile (669 mg, 3.09 mmol), Pd(OAc)2 (53 mg, 0.24 mmol), t-Bu3P.HBF4 (70 mg, 0.24 mmol), and t-BuONa (320 mg, 3.33 mmol) was stirred for 5 hours under reflux in a nitrogen atmosphere. The reaction solution was cooled. Then, insoluble matter was filtered through celite, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (CH2Cl2/MeOH) to obtain an orange amorphous solid. This amorphous solid was dissolved in ethyl acetate (5 mL). A crystal deposited by the addition of 4 N HCl/AcOEt (0.6 mL) was collected by filtration and dried under reduced pressure to obtain (4aS,8aS)-1-(3-chloro-4-cyanophenyl)-3,3-dimethyldecahydroquinoxaline hydrochloride (304 mg, 48%) in a pale orange powder form.

1. temperatureunder reflux in a nitrogen atmosphere
2. temperatureThe reaction solution was cooled
3. filtrationThen, insoluble matter was filtered through celite
4. concentrationthe filtrate was concentrated
5. customThe obtained residue was purified by silica gel column chromatography (CH2Cl2/MeOH)
6. customto obtain an orange amorphous solid
7. filtrationwas collected by filtration
8. customdried under reduced pressure