Chiral nonracemic 3-substituted cis- and trans-4-aminopiperidines, which are precursors of anilidopiperidine analgesics, were obtained by diastereoselective synthesis from 1-methyl- and 1-benzyl-4-[(S)-1-phenylethyl]iminopiperidines, using the following reaction sequence: metalation with lithium diethylamide, alkylation with alkyl halides, and hydride reduction or hydrogenation over Raney nickel. The steric direction of the reaction, three-dimensional structure, preferred conformation, and absolute configuration of the resultant aminopiperidines were determined.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 789-804, May, 2012.
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Grishina, G.V., Luk’yanenko, E.R., Borisenko, A.A. et al. Asymmetric synthesis and stereochemistry of chiral cis- and trans-3-alkyl-4-aminopiperidines. Chem Heterocycl Comp 48, 733–747 (2012). https://doi.org/10.1007/s10593-012-1052-9
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DOI: https://doi.org/10.1007/s10593-012-1052-9