Cesium fluoride → HCID 10535250, compound

Participants

Reaction Steps

To a solution of 4(S)-benzyl-1-(tert-butyldimethyl-silyl)-3(S)-methylazetidin-2-one (557 mg, 1.92 mmol) in MeOH (25 mL) at 0° was added cesium fluoride (439 mg, 2.89 mmol). After 1 h MeOH was evaporated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with H2O and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 50% EtOAc in hexane) to give 4(S)-benzyl-3(S)-methylazetidin-2-one (239 mg, 71% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.35-7.17 (m, 5H), 5.78 (brs, 1H), 3.46 (ddd, J=8.0, 5.9, 2.0 Hz, 1H), 2.98 (dd, J=13.5, 5.9 Hz, 1H), 2.91 (qd, J=7.3, 2.0 Hz, 1H), 2.84 (dd, J=13.5, 8.0 Hz, 1H), 1.26 (d, J=7.3 Hz, 3H).

Provenance & Evidence