Carbon Dioxide → 1-Benzylazetidine-3-carboxylic acid

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A mixture of the disodium salt of N-benzylazetidine-3,3-dicarboxylic acid and sodium carbonate (approximately 2:1 by weight, total weight 7.5 g) were dissolved in 100 ml of a toluene-acetic acid mixture (2/1, v/v), with immediate evolution of carbon dioxide from the sodium carbonate. The mixture was warmed and stirred, and then refluxed over a Dean and Stark water separator. After 1/2hour evolution of carbon dioxide had ceased and 1.5 ml of an acetic acid-water mixture had separated. The slightly hazy solution was cooled to room temperature. A white fluffy solid comprising sodium acetate (3.6 g) was removed by filtration. Distillation of the clear filtrate yielded 4.5 g of N-benzyl-3-carboxy-azetidine.

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