Allylamine → HCID 19600057, compound

Participants

Reaction Steps

To a solution of the crude 2-(3-hydroxymethylfuran-2-yl)ethanol and 1.74 ml (9.96 mmol) of N,N-diisopropylethylamine in 50 ml of dichloromethane, 0.71 ml (9.13 mmol) of methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water and then saturated sodium chloride. After which it was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 50 ml of ethanol, 0.36 g (6.22 mmol) of allylamine and 2.38 ml (13.7 mmol) of N,N-diisopropylethylamine were added, followed by overnight stirring at 80° C. The solvent was distilled off under reduced pressure from the reaction mixture; the resulting crude product was purified by silica gel column chromatog-raphy (hexane/ethyl acetate=9/1 to 6/1) to yield 5-allyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.

Provenance & Evidence