反应详情

温度

-78 °C

Triethylamine trihydrofluoride (0.3 mL, 1.7 mmol) and triethylamine (0.11 mL, 0.8 mL) were dissolved in dichloromethane (30 mL) and cooled to −78° C. To the cooled mixture was added XtalFluor-E (310 mg, 1.4 mmol) and then 1-benzhydryl-3-(2-bromo-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidin-3-ol (Preparation 28, 600 mg, 0.8 mmol). Cooling was removed and the mixture was allowed to warm to room temperature with stirring for 2 hours. The reaction was poured into saturated aqueous sodium carbonate solution (100 mL) and the organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Crude material was chromatographed (40 G Redi-Sep Column) eluting from 100% heptane to 20:80 EtOAc:heptane to afford the intermediate (523 mg, 87%) as a glass. 1HNMR (CDCl3) δ ppm: 7.90 (1H), 7.69-7.66 (3H), 7.47-7.21 (11H), 4.46 (1H), 4.08 (1H), 3.90-3.66 (5H); m/z (Cl) 713 ([M+H]+.

1. temperatureCooling
2. customwas removed
3. temperatureto warm to room temperature
4. additionThe reaction was poured into saturated aqueous sodium carbonate solution (100 mL)
5. customthe organic phase was separated
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customCrude material was chromatographed (40 G Redi-Sep Column)
10. washeluting from 100% heptane to 20:80 EtOAc