Ethyl Acetate → Tert-butyl 3-(2-hydroxyethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

After a solution of tert-butyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (1.7 g) in THF (10 mL) was cooled to −78° C. in an argon atmosphere, a 1.02 M solution of diisobutylaluminium hydride in toluene (17.5 mL) was added dropwise thereto, then, the mixture was stirred at the same temperature for 1 hour, and further stirred at 0° C. for 30 minutes. An aqueous Rochelle salt solution and EtOAc were added the reaction mixture, followed by stirring for 1 hour. After the temperature of the reaction mixture was raised to room temperature, extraction thereof was performed using EtOAc, and the extract was washed with saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=97:3 to 80:20), whereby tert-butyl 3-(2-hydroxyethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (0.83 g) was obtained as a colorless oil.

1. stirringfurther stirred at 0° C. for 30 minutes
2. stirringby stirring for 1 hour
3. extractionextraction
4. washthe extract was washed with saturated brine
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=97:3 to 80:20)

ORD record

ord-c1ff094e27b24f35a87e7e830b8e32cc

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328118B2