Pyridine → HCID 90424176, compound

Participants

Reaction Steps

Slowly add trichloromethyl chloroformate (8.74 mL; 2.0 equiv; 72.84 mmoles) over 10 minutes to a 0° C. solution of 1-[tert-butyl(diphenyl)silyl]oxy-3-imidazol-1-yl-propan-2-ol (13.86 g; 1.0 equiv; 36.42 mmoles) and pyridine (23.56 mL; 8 equiv; 291.36 mmoles) in acetonitrile (500 mL). Stir for 1 hour and then allow the solution to warm to ambient temperature over 1 hour. Add water (50 mL) and concentrate the reaction mixture to 75 mL volume. Add dichloromethane (100 mL), and slowly pour the resulting solution into 50% saturated sodium bicarbonate (200 mL). Separate the layers and further extract the aqueous layer with dichloromethane (3×150 mL). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate. Purification by column chromatography (10% to 100% ethyl acetate in hexanes) affords the desired 6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,6-dihydroimidazo[2,1-c][1,4]oxazin-8-one (9.48 g; 64%) as a light pink gum: MS (m/z): 407(M+1).

Provenance & Evidence