反应详情

温度

0 °C

To a solution consisting of 3-(2-hydroxy-ethyl)-azetidine-1-carboxylic acid tert-butyl ester (0.250 g, 1.24 mmol) and THF (2 mL) at 0° C. was added sodium hydride (0.0459 g, 0.124 mmol). The reaction was stirred at 0° C. for 0.5 h, then treated with tetrabutylammonium iodide (0.0459 g, 0.124 mmol) and 4-chlorobenzyl bromide (0.383 g, 1.86 mmol), warmed to rt and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl (1.0 mL), diluted with ethyl acetate (40 mL) and extracted with 1 N NaOH (40 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give the title compound as a yellow oil (0.302 g, 74%). 1H NMR (d6-DMSO): 7.40 (d, J=8.4 Hz, 2H), 7.32 (d, J=8.4 Hz, 2H), 4.42 (s, 2H), 3.88 (t, J=8.0 Hz, 2H), 3.53-3.44 (m, 2H), 3.40 (t, J=6.2 Hz, 2H), 2.62-2.53 (m, 1H), 1.84-1.74 (m, 2H), 1.36 (s, 9H).

1. temperaturewarmed to rt
2. stirringstirred for 16 h
3. customThe reaction was quenched with saturated aqueous NH4Cl (1.0 mL)
4. additiondiluted with ethyl acetate (40 mL)
5. extractionextracted with 1 N NaOH (40 mL)
6. dry with materialThe organic layer was dried (MgSO4)
7. concentrationconcentrated
8. customThe residue was purified (FCC)