3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol → 3-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane

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Reaction Steps

A mixture of 3-ethynyl-3-hydroxyquinuclidine (5.0g), palladium on calcium carbonate (5% w/w, 0.5 g) and ethanol (200 ml) was stirred under an atmosphere of hydrogen until 900 ml of hydrogen has been consumed. The mixture was filtered and evaporated to give 3-ethenyl-3-hydroxyquinuclidine (5.0 g) as an oil which gave a solid on standing and was used without further purification, m.p. 76°-80° C.; NMR(DMSO-d6): 1.2(1H, m), 1.4-1.6(3H, m), 2.0(1H, m), 2.45-2.85(6H, m), 4.55(1H, s), 5.0(1H, d of d), 5.25(1H, d of d), 6.1(1H, d of d); m/z 154 (M+H).

Provenance & Evidence