Potassium Carbonate → HCID 19432872, compound

Temperature

-30 °C

A stirred solution of (±) 3-(fur-3-yl)-3-hydroxy-1-azabicyclo[2.2.2]octane (D20) (1.20 g, 0.0062 mole) in an acetonitrile (20 ml)/dichloromethane (10 ml) mixture was treated with triethylsilane (5.9 ml, 0.037 mole) and cooled to -30° C. under nitrogen. The solution was treated dropwise over 5 minutes with tin (IV) chloride (1.6 ml, 0.0136 mole) and then allowed to warm to room temperature over 0.5 h, before pouring into excess potassium carbonate solution and extracting with ethyl acetate (2×60 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue eluted through a short basic alumina column with ether. The yellow oil obtained was then chromatographed on silica gel eluting with 0 to 20% methanol/chloroform to give the title compound (E10) as a pale yellow oil (150 mg, 10%). This was converted into its hydrochloride salt and recrystallised from methanol/ether m.p. 179°-182° C.

1. temperatureto warm to room temperature over 0.5 h
2. extractionextracting with ethyl acetate (2×60 ml)
3. dry with materialThe combined extracts were dried (Na2SO4)
4. concentrationconcentrated in vacuo
5. washthe residue eluted through a short basic alumina column with ether
6. customThe yellow oil obtained
7. customwas then chromatographed on silica gel eluting with 0 to 20% methanol/chloroform

ORD record

ord-fced136b9ef647e3badf3da7b8c7dac9

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05541194