反应详情

A mixture of (+/−)1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (500 mg, 1.58 mmol), 3,5-Bis(trifluoromethyl)benzylamine (423 mg, 1.74 mmol) and titanium(IV) isopropoxide (0.59 ml, 1.97 mmol) in diglyme (2 ml) is stirred at room temperature for 22 hours. The mixture is diluted with methanol (7 ml) and treated with sodium borohydride (90 mg, 2.37 mmol), then stirred at room temperature for 6 hours. The mixture is treated with 0.1N aqueous NaOH (15 ml) and stirred for 10 minutes, then filtered. The filter cake is washed with 1:1 ethanol:diethyl ether. The filtrate is diluted with water (70 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated to an oil. The oil is purified by silica gel column chromatography (eluent, 15% ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 543 (M+H).

1. stirringstirred at room temperature for 6 hours
2. stirringstirred for 10 minutes
3. filtrationfiltered
4. washThe filter cake is washed with 1:1 ethanol
5. additionThe filtrate is diluted with water (70 ml)
6. extractionextracted with ethyl acetate (2×30 ml)
7. washThe combined organic extracts are washed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated to an oil
10. customThe oil is purified by silica gel column chromatography (eluent, 15% ethyl acetate in hexanes)