反应详情

温度

-78 °C

(2S,4R)-tert-butyl 4-hydroxy-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate, 1-2c (1.5 g, 3.3 mmol) was added as a solid to a solution of bis(2-methoxyethyl)aminosulfur trifluoride (0.91 mL, 5.0 mmol) in 15 mL CH2Cl2 cooled to −78° C. Reaction was stirred at −78° C. for two hours and then warmed to room temperature and stirred for 2 hours. Reaction was poured into saturated sodium bicarbonate solution and stirred until bubbling ceased. Layers were separated and aqueous layer washed one time with CH2Cl2. Combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to give a brown oil. The oil was chromatographed on silica gel with 5% MeOH/CH2Cl2 to yield 4-(2-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidin-2-yl)-1H-imidazol-5-yl)phenylboronic acid as a tan solid (0.46 g, 37%).

1. customReaction
2. temperaturewarmed to room temperature
3. stirringstirred for 2 hours
4. customReaction
5. stirringstirred
6. customuntil bubbling
7. customLayers were separated
8. washaqueous layer washed one time with CH2Cl2
9. washCombined organics were washed with brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customto give a brown oil
14. customThe oil was chromatographed on silica gel with 5% MeOH/CH2Cl2