Hydrochloric Acid → Tert-butyl 3-[(6-chloro-2-methylpyridin-3-yl)methoxy]azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (170 mg of 60%, 4.26 mmol) was suspended in tetrahydrofuran (12 mL) and cooled to 0° C. tert-Butyl 3-hydroxyazetidine-1-carboxylate (246 mg, 1.420 mmol) was added and the slurry was stirred for 30 minutes at 0° C. 3-(Bromomethyl)-6-chloro-2-methylpyridine (Example 421, Step 2) (313 mg, 1.420 mmol) was added and the solution was heated to 50° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water, acidified with 1 N hydrochloric acid, and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, concentrated and purified via silica gel chromatography (0-2% methanol in ethyl acetate) to afford the title compound.

Provenance & Evidence