Methylamine → 3-Methyl-7-p-toluenesulfonyl-3,7-diazabicyclo[3.3.0]oct-1(5)-ene

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Reaction Steps

To a solution of 1-p-toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline (6.1 g) was dissolved in acetonitrile (70 ml), 40% methylamine aqueous solution (1.5 ml) and anhydrous potassium carbonate powder (16 g) were added and stirred for 2 hours at room temperature. The solid was filtered off and the filtrate was purified by silicagel column chromatography to yield 3-methyl-7-p-toluenesulfonyl-3,7-diazabicyclo[3.3.0]oct-1(5)-ene (0.82 g, yield 20%). 0.8 g of this compound and 0.8 g of phenol were refluxed in 48% hydrobromic acid (15 ml) for 5 hours. The reaction mixture was washed with chloroform (20 ml×3), decolorized with active charcoal. The solvent was distilled off and washed with ethanol-ethylether (1:1) to give the title compound (0.5 g, yield 60%).

Provenance & Evidence