Methyl iodide → 1-Benzhydryl-3-ethyl-3-methoxyazetidine

Participants

Reaction Steps

To a DMF (50 mL) solution of 1-benzhydryl-3-ethylazetidin-3-ol (2.18 g, 8.15 mmol), methyl iodide (0.51 mL, 8.15 mmol) and 60% sodium hydride (0.65 g, 16.31 mmol) were added at 0° C. under a nitrogen stream, and the mixture was stirred for 1.5 hours at the same temperature. This reaction liquor was poured onto ice water, and the mixture was extracted with ethyl acetate. The extract was washed with ice water and saturated brine in this order, and then dried over anhydrous sodium sulfate. Sodium sulfate was separated by filtration, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 25S, ethyl acetate/n-hexane=1/9-4/6), to obtain the title compound (1.18 g, 52%) as an oily matter.

Provenance & Evidence