Sodium Iodide → 3-Octylpyrrolidine

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Reaction Steps

A mixture of 0.15 mol. of anhydrous sodium iodide and 150 ml. of dry methyl ethyl ketone is heated for 30 minutes at 80°, 0.1 mol of 1-chloroheptane is added, and heating is continued for 10 hours with periodic shaking. The cooled solution is filtered and most of the solvent is distilled off. The residue is diluted with 150 ml. of benzene, the solution is washed with water, 5% sodium thiosulfate, water, and dried over magnesium sulfate. The filtrate solution is concentrated to 100 ml., 0.12 mol. of triphenyl phosphine is added and the mixture is heated for 10 hours at 80°. The benzene is distilled off and the residue is triturated with ether, filtered and dried. A solution of 25 mmoles of this heptyltriphenyl phosphonium iodide in 40 ml. of dried DMF is mixed rapidly with 20 mmoles of sodium methoxide and the mixture is stirred for one hour at room temperature. The solution of heptylidenetriphenyl phosphorane is cooled with ice water and mixed with a solution of the 15 mmoles of the 1-(t-butoxycarbonyl)-3-pyrrolidinecarboxaldehyde obtained in step B, dissolved in 10 ml. of DMF and the mixture is stirred at 20° for 20 hours. After dilution with water, the desired 1-(t-butoxycarbonyl)-3-(1-octenyl)pyrrolidine is extracted with ethyl acetate. The ethyl acetate extract is concentrated to dryness in vacuo and the residue is hydrogenated in the presence of 10% palladium on charcoal, then treated with trifluoroacetic acid as in step E of the same example to obtain 3-octylpyrrolidine.

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