[Na][Na].[CH2:3]([N:10]1[CH2:13][C:12](C(O)=O)([C:14]([OH:16])=[O:15])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>C1(C)C(CC(O)=O)=CC=CC=1.O>[CH2:3]([N:10]1[CH2:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
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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