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Synthesis and three-dimensional structures of 3-(α-amino- and α-hydroxybenzyl)quinuclidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Substituted quinuclidines that contain a hydroxy or amino group in the side chain were synthesized by reduction of 3-benzoyl- and 3-benzoylmethylquinuclidines and their oximes. It is shown that the reduction of the ketones takes place stereospecifically to give one diastereomeric alcohol in both cases, whereas mixtures of diastereomeric 3-(α-aminobenzyl)quinuclidines are formed in the hydrogenation of their oximes. The configurations of the substances obtained were established on the basis of data from the PMR spectra.

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Literature cited

  1. C. A. Grob, U.S. Patent No. 2917515; Chem. Abstr., 54, 8862 (1960).

    Google Scholar 

  2. S. J. Sallay and S. J. Childress, U.S. Patent No. 3534053; Ref. Zh. Khim., 17N465P (1971).

  3. R. J. Abraham and K. G. R. Pachlev, Mol. Phys., 165 (1964).

  4. K. F. Turchin, E. E. Mikhlina, V. Ya. Vorob'eva, A. D. Yanina, Yu. N. Sheinker, and L. N. Yakhontov, Dokl. Akad. Nauk SSSR, 192, 823 (1970).

    Google Scholar 

  5. V. Ya. Vorob'eva, K. F. Turchin, E. E. Mikhlina, V. A. Bondarenko, A. I. Ermakov, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 10, 1377 (1977).

    Google Scholar 

  6. M. É. Kaminka, E. E. Mikhlina, V. Ya. Vorob'eva, A. D. Yanina, N. A. Komarova, M. D. Mashkovskii, and L. N. Yakhontov, Khim.-farm. Zh., No. 6, 48 (1976).

    Google Scholar 

  7. R. J. Mauvernay, N. Busch, T. Jassav, and A. Menteil, West German Patent No. 2323303; Chem. Abstr., 80, 70722 (1974).

    Google Scholar 

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119021, Moscow

    V. Ya. Vorob'eva, E. E. Mikhlina, K. F. Turchin, Yu. N. Sheinker & L. N. Yakhontov

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  1. V. Ya. Vorob'eva
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  2. E. E. Mikhlina
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  3. K. F. Turchin
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  4. Yu. N. Sheinker
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  5. L. N. Yakhontov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 381–385, March, 1983.

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Vorob'eva, V.Y., Mikhlina, E.E., Turchin, K.F. et al. Synthesis and three-dimensional structures of 3-(α-amino- and α-hydroxybenzyl)quinuclidines. Chem Heterocycl Compd 19, 310–314 (1983). https://doi.org/10.1007/BF00513268

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  • DOI: https://doi.org/10.1007/BF00513268

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