3-Pyridinemethanol → Pyridin-3-ylmethyl 3-ethynylazetidine-1-carboxylate

Participants

Reaction Steps

To a solution of CDI (1.14 g, 7.02 mmol) in THF (15 ml) was added pyridine-3-methanol (0.68 ml, 7.0 mmol) at 0° C., and the reaction was stirred at room temperature for 1 hour. A solution of 3-ethynylazetidine (TFA salt) (250 mg, 1.40 mmol) and triethylamine (0.98 ml, 7.0 mmol) in THF (3 ml) was added to the reaction mixture, followed with DBU (0.42 ml, 2.8 mmol). After 3 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, then dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with methanol/ethyl acetate to give pyridin-3-ylmethyl 3-ethynylazetidine-1-carboxylate. LRMS (ESI) calculated for C12H13N2O2 [M+H]+, 217.1; found 217.1.

Provenance & Evidence