Water → (3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol

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Reaction Steps

The acetate 49 (179 g, 0.926 mol) was treated with a solution of NaH (60% dispersion in oil, 100 mg, 2.7 mmol) in methanol (900 ml). After stirring for 2 hours at reflux, water (20 ml) was added and the solution concentrated. The residue was treated with ether and the white solid obtained was filtered off, dissolved in ethanol (2 L) and water (200 ml). The mixture was evaporated to dryness and dried under vacuum to give the (3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol 50 as a white solid (138 g, 98%).

Provenance & Evidence