Pyrrolidine → 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-pyrrolidino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole

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Reaction Steps

A mixture of 150 mg (0.687 m mol) of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole, 63 μl (0.756 m mol) of pyrrolidine and 2 ml of ethanol was refluxed with stirring for 31 hours. After the solvent was distilled off, the residue was subjected to a preparative silica gel thin layer chromatography using a developing solvent of ethyl acetate-methanol (1:1 (v/v)) to obtain 120 mg (yield: 60%) of the intended compound. A part of the obtained compound was dissolved in dry ether and added with HCl--EtOH to obtain hydrochloride of the intended compound as pale yellow crystals.

Provenance & Evidence