Potassium Hydroxide → 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

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Reaction Steps

The above oil containing (-)-3-ethynyl-3-butyryloxyquinuclidine was treated with a solution of potassium hydroxide (2.24 g) in methanol (50 ml). The mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and deionised water (2 ml) was added to the residue to give a solid. The solid was collected by filtration, washed with water (2×2 ml) and dried under vacuum over phosporus pentoxide to give (-)-3-ethynyl-3-hydroxyquinuclidine (611 mg) as a solid, m.p. 199°-202° C., [α]19D =-56.1° (C=1.02, methanol).

Provenance & Evidence