tert-Butyldimethylsilyl chloride → HCID 10540376, compound

Participants

Reaction Steps

To a solution of 4(S)-benzylazetidin-2-one (400 mg, 2.48 mmol) in CH2Cl2 (8 mL) was added DIEA (648 μL, 3.72 mmol), followed by tert-butyldimethylsilyl chloride (411 mg, 2.73 mmol). The reaction mixture was stirred for 16 h at room temperature. The CH2Cl2 was evaporated and the residue was purified by flash chromatography (SiO2, 12% EtOAc in hexane) to give 4(S)-benzyl-1-(tert-butyldimethylsilyl)azetidin-2-one (647 mg, 95% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.34-7.15 (m, 5H), 3.77-3.70 (m, 1H), 3.25 (dd, J=13.5, 3.5 Hz, 1H), 2.99 (dd, J=15.5 Hz, 5 Hz, 1H), 2.70 (dd, J=15.5, 2.5 Hz, 1H), 2.59 (dd, J=13.5, 11 Hz, 1H), 1.01 (s, 9H), 0.31 (s, 3H), 0.29 (s, 3H).

Provenance & Evidence