Sodium ethoxide → (1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octane

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Reaction Steps

(1R, 2R, 3S)-2-hydroxymethyl-3-(3,4-dichlorophenyl)tropane tosylate (2.5 g, 5.5 mmol) was dissolved in anhydrous ethanol (20 ml). Sodium ethoxide in ethanol (2.4 ml, 2.5M, 6 mmol) was added and the reaction mixture was refluxed for 72 hours. The solvent was evaporated off. The residue was stirred with water and ether and extracted three times with ether (3×50 ml) and dried over MgSO4. Evaporation of the solvent yields 1.75 g of the title compound. The product was purified by column chromatography on silica using EtOAc:Et3N (99:1). Yield 1.24 g.

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