Pyridine → HCID 86606460, compound

Participants

Reaction Steps

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and benzyl chlorocarbonate (1.57 mL) was added dropwise thereto. After stirring at room temperature for 2 hrs, pyridine (0.65 mL) and benzyl chlorocarbonate (1.28 mL) were further added. After stirring at room temperature for 5 days, pyridine (0.81 mL) was further added under ice-cooling, and a solution of benzyl chlorocarbonate (1.43 mL) in ethyl acetate (5 mL) was slowly added dropwise. The reaction solution was stirred at room temperature for 2 hrs, and added ethyl acetate (50 mL), then, washed with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 2 hrs, diethyl ether (10 mL) was added, and the depositting solid was collected by filtration. The solid was dried under reduced pressure to give title compound as white solid (1.99 g).

Provenance & Evidence