反应详情

Add methanesulfonyl chloride (0.745 g, 6.50 mmol) to a cool (0° C.) solution of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.4 g, 5.0 mmol) and triethylamine (1.26 g, 12.5 mmol) in dichloromethane (20 mL). Warm to room temperature and stir for 1 hour. Remove solvents, transfer crude of methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester residue to a sealed tube, add tetrahydrofuran (30 mL), azetidine (2.0 g, 35.5 mmol), and heat at 60° C. overnight. Wash the crude organic material with 1N HCl. Separate layers and add 5N NaOH to the aqueous layer until it is basic. Extract the aqueous layer with diethyl ether (2×50 mL), dry the organic extracts over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 10% ammoniated methanol in dichloromethane to give 4-(2-azetidin-1-yl-ethyl)-2-(4-bromo-phenyl)-5-methyl-oxazole (1.22 g, 72%): mass spectrum (m/e): 323 (M+1).

1. temperatureheat at 60° C. overnight
2. washWash the crude organic material with 1N HCl
3. additionSeparate layers and add 5N NaOH to the aqueous layer until it
4. extractionExtract the aqueous layer with diethyl ether (2×50 mL)
5. dry with materialdry the organic extracts over Na2SO4
6. filtrationfilter
7. concentrationconcentrate
8. customPurify on silica gel eluting with 10% ammoniated methanol in dichloromethane