Sodium hydride → HCID 66974099, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence