Abstract
Three isomeric dimethyl esters of 4-hydroxypiperidine-2, 6-dicarboxylic acid have been isolated. The spatial structures of all three isomeric esters and of the acids corresponding to them have been established on the basis of NMR spectra. It has been shown that while the isomers I and II exist in the form of only one conformation each, isomer III in neutral and acid media apparently consists of an equilibrium mixture of two (or more) conformers. The information obtained on the spatial structure of the isomeric esters shows that the cyclization of these compounds with benzylamine and p-nitrobenzaldehyde takes place with the inversion of the piperidine ring.
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Turchin, K.F., Nikitskaya, E.S., Sheinker, Y.N. et al. The spatial structure of the isomeric dimethyl esters of 4-hydroxypiperidine-2, 6-dicarboxylic acid. Chem Heterocycl Compd 5, 485–490 (1969). https://doi.org/10.1007/BF00470265
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DOI: https://doi.org/10.1007/BF00470265