p-Toluenesulfonic acid monohydrate → Pyrrolidine, 1-[2-(5-fluoro-3,4-dihydro-2-naphthalenyl)ethyl]-

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Reaction Steps

To a solution of 5-fluoro-1,2,3,4-tetrahydro-2-[2-(1-pyrrolidinyl)ethyl]-1-naphthalenol (20.0 g) in toluene (250 ml) was added p-toluenesulfonic acid. monohydrate (16.2 g), and the mixture was refluxed overnight. After cooling, the reaction solution was washed successively with 1N aqueous sodium hydroxide solution, water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=5:1), and the fractions containing the desired compound were combined, concentrated under reduced pressure to give the desired compound (12.6 g), as an oily product.

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