Pyridine → HCID 90060182, compound

Temperature

0 °C

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.

1. temperatureWhile maintaining the reaction temperature at 0° C.
2. temperatureWhile maintaining the reaction temperature at 0° C.
3. stirringthe mixture was stirred at room temperature for 15 hours
4. customthe reaction
5. extractionthe mixture was extracted with dichloromethane
6. washThe organic layer was washed with 1.0 M hydrochloric acid, water
7. dry with materiala saturated brine, dried over anhydrous sodium sulfate
8. filtrationfiltered
9. distillationThe solvent was distilled off
10. customThe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1, Rf=0.6)

ORD record

ord-4b7add7369964de6bce302d4f34abcab

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2