Water → (Z)-3-Acetylmethylene-1-azabicyclo[2.2.2]octane oxalate

To a solution of 3-quinuclidinone (2.0 g, 16 mmol) and potassiumhydroxide (1.93 g, 30 mmol) in water cooled to -5° C. (7.7 ml), dimethyl 2-oxopropylphosphonate (4.9 g, 30 mmol) was added dropwise. The reaction mixture was stirred at a temperature between 0° C. to -5° C. for 90 hours. The reaction mixture was quenched with 1 M hydrochloric acid solution (50 ml), rinsed three times with ether, made basic with solid potassiumcarbonate and extracted with methylenchloride (5×50 ml). The solvent was removed after drying over magnesiumsulfate. The crude compound was crystallised as the oxalate salt from ethanol (100 ml) and then recrystallised from ethanol (50 ml) to give the title compound in 21% yield. M.p. 189-190° C. (Compound 1).

1. additionwas added dropwise
2. customThe reaction mixture was quenched with 1 M hydrochloric acid solution (50 ml)
3. washrinsed three times with ether
4. extractionextracted with methylenchloride (5×50 ml)
5. customThe solvent was removed
6. dry with materialafter drying over magnesiumsulfate
7. customThe crude compound was crystallised as the oxalate salt from ethanol (100 ml)
8. customrecrystallised from ethanol (50 ml)

ORD record

ord-b694d829d39e4ecc8de3e3e301f5ea67

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05936088