Potassium Hydroxide → 6-(3-Pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene

To ethyl 6-hydroxy-6-(3-pyridinyl)-3-azabicyclo[3.2.1]octane-3-carboxylate (1.10 g, 4.0 mmol) was added thionyl chloride (5 ml) and the mixture was heated to reflux for 1 h under nitrogen. Thionyl chloride was removed by azeotropic rotary evaporation with toluene to give a dark brown oil, which was suspended in a 20% solution of potassium hydroxide in ethanol (10 ml) and refluxed for 18 h. The reaction mixture was cooled to room temperature and concentrated by rotary evaporation. Then saturated sodium chloride solution (10 ml) was added. The mixture was filtered. The collected solids were washed with chloroform (25 ml), and the filtrate was extracted with chloroform (3×25 ml). The combined chloroform extracts were dried over sodium sulfate, filtered, concentrated by rotary evaporation, and distilled on a Kugelrohr apparatus to yield a light brown oil (350 mg, 47%).

1. temperaturethe mixture was heated
2. temperatureto reflux for 1 h under nitrogen
3. customThionyl chloride was removed by azeotropic rotary evaporation with toluene
4. customto give a dark brown oil, which
5. temperaturerefluxed for 18 h
6. concentrationconcentrated by rotary evaporation
7. additionThen saturated sodium chloride solution (10 ml) was added
8. filtrationThe mixture was filtered
9. washThe collected solids were washed with chloroform (25 ml)
10. extractionthe filtrate was extracted with chloroform (3×25 ml)
11. dry with materialThe combined chloroform extracts were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated by rotary evaporation
14. distillationdistilled on a Kugelrohr apparatus

ORD record

ord-673876cf7b634c0dac334290b5cfb322

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897611B2