Hydrochloric Acid → 3-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane

Under an argon atmosphere, a solution of 3-quinuclidinone (1.25 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) was added over 15 minutes to a 1 M solution of vinylmagnesium bromide in tetrahydrofuran (20 mL, 20 mmol) at 0° C. to 5° C., stirred at room temperature for 24 hours, cooled to 0° C., and acidified to pH 1 with 6 M hydrochloric acid. The mixture was stirred for 15 minutes, basified to pH 10 with 25% aqueous sodium hydroxide, extracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL), combined the organic layers, dried (MgSO4), evaporated under reduced pressure and purified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15) to obtain the title compound (830 mg, 5.4 mmol, 54%).

1. temperaturecooled to 0° C.
2. stirringThe mixture was stirred for 15 minutes
3. extractionextracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL)
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. custompurified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15)

ORD record

ord-2894992ed5bd46819951138fe08069e2

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703502B2