Diethyl Ether → Benzyl 3-hydroxy-3-methylazetidine-1-carboxylate

Participants

Reaction Steps

To a 3.0 M solution of methylmagnesium bromide in Et2O (0.98 mL, 2.92 mmol), at 0° C., was added a solution of 3-oxoazetidine-1-carboxylic acid benzyl ester (0.5 g, 2.44 mmol) in anhydrous THF (5 mL) dropwise over 5 min under argon. The reaction mixture was stirred for 18 h at room temperature, and then quenched by addition of a saturated aqueous solution of NH4Cl (2.5 mL) and water (5 mL). The aqueous phase was extracted with EtOAc (10 mL) The organic layer was separated, dried over sodium sulphate and concentrated in vacuo to give 3-Hydroxy-3-methylazetidine-1-carboxylic acid benzyl ester as a colourless oil (0.54 g, 99%). LCMS (Method A): RT=3.60 min, [M+H]+ 221.9

Provenance & Evidence