Carbon Dioxide → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

Participants

Reaction Steps

Three drops of 5M hydrochloric acid was added to a stirred mixture of 2,5-dimethoxytetrahydrofuran (16.5 g) and water (70 ml). After 10 minutes a mixture of benzylamine (13.6 ml) and 5M hydrochloric acid (30 ml) were added followed by the immediate addition of a mixture of 1,3-acetonedicarboxylic acid (18.2 g) and sodium acetate (10 g) in water (100 ml). After stirring at room temperature for 3 days, during which carbon dioxide was evolved, the mixture was basified to pH8 and extracted with ethyl acetate (×3). The combined extracts were dried (MgSO4) and evaporated under reduced pressure. Chromatography [SiO2; hexane:ethyl acetate] to give 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (11.2 g).

Provenance & Evidence