Sodium Hydroxide → HCID 23121981, compound

80% Aluminum lithium hydride (0.36 g, 7.5 mmol) was suspended in tetrahydrofuran (10 mL). A solution of 1,1-dimethylethyl N-[2-(3,6-dihydropyridin-1(2H)-yl)ethyl]carbamate (0.68 g, 3.0 mmol) in tetrahydrofuran (10 mL) was added dropwise thereto at room temperature over 10 minutes, and the mixture was refluxed for 3 hours. The reaction solution was cooled to room temperature, and then a 1 N aqueous sodium hydroxide solution (20 mL) was added portionwise thereto. Insolubles were filtered off through a Celite, and the Celite was washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure, and the residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=19:1 to ethyl acetate) to obtain the title compound (0.18 g, yield 42%).

1. temperaturethe mixture was refluxed for 3 hours
2. filtrationInsolubles were filtered off through a Celite
3. washthe Celite was washed with tetrahydrofuran
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=19:1 to ethyl acetate)

ORD record

ord-5c039b7780d14a95beb719eb36551ce1

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795267B2