反应详情

To a stirred ice-cooled solution of 987 mg of trans-6-amino-3-chloro-α-cyclopropyletheayl-α-(trifluoromethyl)benzyl alcohol (from Example 5, Part B) in 50 mL of dry ether was added 0.350 mL of dry pyridine aid 1.66 g of α-bromopropionyl bromide. The cooling bath was removed and then after 30 min at ambient temperature, the reacation mixture was diluted with ether, washed with water and aqueous sodium bicarbonate, dried and evaporated. The residte was dissolved in 50 mL of dry DMF, 2.35 g of lithium iodide and 2.3 g of cesium carbonate was added, and the resulting heterogeneous mixture was stirred at room temperature for 3 days. The reaction mixture was then poured onto water and extracted twice with ether. The combined extracts were washed with water and brine, dried and evaporated to crude product. The title compound was obtained by crystallization from ethyl acetate/hexanes, and recrystallization from ethyl acetate afforded 650 mg of pure title corpound: mp 171-172°; HRMS: Calcd. for C16H168NO2F3Cl (M+H)+ : 346.082166. Found: 346.080681: mp 147-147.5°; HRMS: Calcd. for C17H18NO2F3Cl (M+H)+ : 360.097816. Found: 360.097869

1. customThe cooling bath was removed
2. additionthe reacation mixture was diluted with ether
3. washwashed with water and aqueous sodium bicarbonate
4. customdried
5. customevaporated
6. dissolutionThe residte was dissolved in 50 mL of dry DMF
7. addition2.35 g of lithium iodide and 2.3 g of cesium carbonate was added
8. additionThe reaction mixture was then poured onto water
9. extractionextracted twice with ether
10. washThe combined extracts were washed with water and brine
11. customdried
12. customevaporated to crude product