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Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using 1H NMR Spectroscopy

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Abstract

Using the 1H NMR spectroscopic method it has been shown that 7-alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and 7-alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonanes exist in deuterochloroform solution in a double chair conformation. 7-(3-Butoxypropyl)-3-oxa-7-azabicyclo[3.3.1]nonan-9-ol is a 1:1 mixture of the two stereoisomeric alcohols. One of them exists in a double chair conformation having an equatorial hydroxyl group with relation to the piperidine ring and the other in a chair-boat conformation having an axial hydroxyl group which involves an intramolecular hydrogen bond with the unshared electron pair of the nitrogen atom.

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Authors and Affiliations

  1. Ministry of Education and Science for the Kazakhstan Republic, A. B. Bekturov Institute for Chemical Sciences, Almaty, 480100

    S. G. Klepikova, V. K. Yu, E. E. Fomicheva, R. D. Mukhasheva, K. D. Praliev & V. A. Solomin

  2. Chemistry Faculty, Oklahoma State University, Stillwater, 74078, USA

    K. D. Berlin

Authors
  1. S. G. Klepikova
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  2. V. K. Yu
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  3. E. E. Fomicheva
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  4. R. D. Mukhasheva
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  5. K. D. Praliev
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  6. V. A. Solomin
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  7. K. D. Berlin
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Klepikova, S.G., Yu, V.K., Fomicheva, E.E. et al. Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using 1H NMR Spectroscopy. Chemistry of Heterocyclic Compounds 39, 1376–1384 (2003). https://doi.org/10.1023/B:COHC.0000010656.65900.72

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  • DOI: https://doi.org/10.1023/B:COHC.0000010656.65900.72

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