Carbon Dioxide → HCID 19610921, compound

Participants

Reaction Steps

(±) 3-Azido-1-azabicyclo[2.2.2]octane oxalate salt (D25) (200 mg, 0.0083 mole) in acetone (20 ml) was treated with acetylene dicarboxylic acid (500 mg, 0.0044 mole) and concentrated in vacuo to produce a homogenous gum. Xylene (20 ml) was added and the solution heated to reflux for 10 min when the suspension rapidly darkened and evolved carbon dioxide. The xylene was then removed in vacuo and the residue partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum. Chromatography on alumina in a gradient of 5-30% methanol in ethyl acetate afforded the title compound (E35) which crystallised from 40-60° petrol as needles m.p. 62-65° C. (60 mg, 0.0034 moles, 40%).

Provenance & Evidence