Pyridine → HCID 90060182, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 3-methylamino-propan-1-ol (343.4 mg, 3.85 mmol) was dissolved in dichloromethane (5.0 mL), and triethylamine (588.2 μL, 4.24 mmol) was added. The mixture was cooled to 0° C. While maintaining the reaction temperature at 0° C., 1-chloroethyl chloroformate (415.7 μL, 3.85 mmol) was then added and the mixture was stirred for 1 hour. While maintaining the reaction temperature at 0° C., acetic anhydride (400 μL, 4.24 mmol) and pyridine (314.4 μL, 3.85 mmol) were then added, and the mixture was stirred at room temperature for 15 hours. After completing the reaction, the mixture was extracted with dichloromethane. The organic layer was washed with 1.0 M hydrochloric acid, water, and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1, Rf=0.6) to obtain 479.5 mg (52% yield) of 3-[(1-chloro-ethoxycarbonyl)-methyl-amino]-propyl acetate.

Provenance & Evidence