Pyridine → 4-Chloromethyl-4-methyl-oxazolidin-2-one

Participants

Reaction Steps

A solution of 2-(tert-butoxycarbonylamino)-2-methyl-1,3-propanediol (2.28 g, 11.1 mmol) in CH2Cl2 (100 ml) and pyridine (2.0 ml, 25 mmol) was cooled to 0° C. and sulfuryl chloride (1.0 ml, 12 mmol) in CH2Cl2 (20 ml) was added dropwise over 15 min. The solution was warmed to RT over 4 h, diluted with diethyl ether (300 ml), washed with 3× 100 ml 5% NaHSO4, 3× 100 ml sat. NaHCO3, 1× 100 ml sat. NaCl, dried on MgSO4, and evaporated. The crude material was purified by flash chromatography (30-100% EtOAc in hexanes) to afford the title compound as a clear oil (470 mg, 3.14 mmol, 28.3%). 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 3H), 3.55 (s, 2H), 4.12 (d, 1H, J=9.2 Hz), 4.33 (d, 1H, J=8.8 Hz), 5.9 (br s, 1H). APCI/ESI calculated for C5H8ClNO2: 149.02. Found: 150 (MH+).

Provenance & Evidence