Potassium Carbonate → HCID 19432872, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence