反应详情

To a solution of 4-methyl-N-[4-(methylsulfonyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide (28 g, 66 mmol) in anhydrous N,N-dimethylacetamide (DMA) (0.53 L) was added sodium tert-butoxide (15 g, 15 mmol) and stirred at room temperature for 30 min under N2. (4S,5S)-4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide (15 g, 99 mmol) in anhydrous DMA (2.0 ml) was added to the solution and stirred at 70° C. for 2.0 h. The reaction mixture was cooled to room temperature and added 2N HCl (0.14 L) and concentrated on a rotary evaporator. To this residue was added anhydrous tetrahydrofuran (THF) (140 ml) and 5N HCl (0.14 L) and stirred at 60° C. for 90 min. The mixture was diluted with ethyl acetate and washed with water, saturated NaHCO3 and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (9:1 to 1:1 dichloromethane:ethyl acetate) to give an atropisomeric mixture of title compound as a white solid (22.5 g, 69%).

1. stirringstirred at 70° C. for 2.0 h
2. temperatureThe reaction mixture was cooled to room temperature
3. concentrationconcentrated on a rotary evaporator
4. additionTo this residue was added anhydrous tetrahydrofuran (THF) (140 ml) and 5N HCl (0.14 L)
5. stirringstirred at 60° C. for 90 min
6. additionThe mixture was diluted with ethyl acetate
7. washwashed with water, saturated NaHCO3 and brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated on a rotary evaporator
10. customThe resulting residue was purified by silica-gel column chromatography (9:1 to 1:1 dichloromethane:ethyl acetate)
11. customto give