Hydrochloric Acid → (+)-Epibatidine dihydrochloride

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Reaction Steps

Racemic-epibatidine 19 (42 mg, 0.2 mmol) was mixed with 77 mg (0.7 mmol) freshly prepared ethyl formamidinate hydrochloride and 129 mg (1.0 mmol) diisopropyl ethylamine in 1 ml acetonitrile. After stirring at room temperature for 48 hours, the mixture was acidified with 1.0 M hydrogen chloride in ether. After evaporation in vacuo, the residue was separated on silica gel preparative thin layer chromatography, using a solvent system of 25% methanol in chloroform, to give 25 mg of the compound 45 as a hygroscopic solid. Yield 36%. MS(CI), 236, 238 (free base M+1). H1 -NMR (CD3OD). δ 3.40 (M, 1H, H2).

Provenance & Evidence