Water → HCID 68916809, compound

Temperature

60 °C

To a solution of benzyl 4-hydroxy-1-piperidinecarboxylate (1.0 g) in toluene/aqueous 2N sodium hydroxide solution (10 mL/10 mL) was added tetrabutylammonium bromide (550 mg) and methoxyethyl bromide (1.2 mL) and the mixture was stirred at 60° C. for 2.5 hours and then stirred at 80° C. for 17 hours. To the reaction mixture was added sodium hydroxide (0.95 g) and methoxyethyl bromide (1.2 mL) and the mixture was stirred at 80° C. for 24 hours. After cooling to room temperature, to the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=75/25 to 40/60) to give benzyl 4-(2-methoxyethoxy)-1-piperidinecarboxylate (266 mg, yield: 21%) as a pale yellow liquid.

1. stirringstirred at 80° C. for 17 hours
2. stirringthe mixture was stirred at 80° C. for 24 hours
3. temperatureAfter cooling to room temperature, to the reaction mixture
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with a saturated brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo
9. customthe resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=75/25 to 40/60)

ORD record

ord-366cdb6245f949c8b9a07012244ac215

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188097B2