Conclusion
The main product of the benzoylation of the hydrochloride of t-2-methyl-t-5-hydroxy-r-9-H-cis-decahydroquinoline, which exists in the conformation with the intramolecular H-bond, is the amidoester which can form a stable 1∶1 complex with benzoic acid having the strong OH... O=CN H-bond. The amidoester thereby exists in the conformation with the diaxial disposition of the substituents in the α,α′-positions of the piperidine ring.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1056–1060, May, 1988.
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Espenbetov, A.A., Struchkov, Y.T., Kuz'mina, N.Y. et al. Stereochemistry of nitrogen heterocycles. 70. Conformation of 1-benzoyl-t-2-methyl-t-5-benzoyloxy-r-9-h-cis-decahydroquinoline and the nature of its complex with benzoic acid. Russ Chem Bull 37, 922–926 (1988). https://doi.org/10.1007/BF00957061
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DOI: https://doi.org/10.1007/BF00957061