反应详情

温度

85 °C

A mixture of 3-methanesulfonyloxyazetidine-1-carboxylic acid tert-butyl ester (4.00 g, 15.9 mmol), 4-iodopyrazole (3.1 g, 15.9 mmol), potassium carbonate (2.85 g, 20.6 mmol) and 18-crown-6 (400 mg) in dry DMF (15 mL) was heated at 85° C. for 24 h. The reaction mixture was cooled to RT, poured into water and extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with hexanes/dichloromethane/ethyl acetate (8:1:1) to give the pure title compound. 1H NMR (300 MHz, CDCl3): δ=1.47 (s, 9H), 4.29 (m, 2H), 4.36 (m, 2H), 5.05 (m, 1H), 7.59 (s, 1H), 7.60 (s, 1H).

1. temperatureThe reaction mixture was cooled to RT
2. extractionextracted with EtOAc (3×20 mL)
3. washThe combined organic layers were washed with water (2×10 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel eluting with hexanes/dichloromethane/ethyl acetate (8:1:1)