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Russian Journal of Organic Chemistry

, Volume 52, Issue 1, pp 87–91 | Cite as

Synthesis of 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones

  • A. Yu. Mandzhulo
  • N. A. Mel’nichuk
  • V. N. Fetyukhin
  • M. V. Vovk
Article

Abstract

N-Boc-protected 8-azaspiro[bicyclo[3.2.1]octane-3,2′-oxirane] reacted with primary aliphatic amines through opening of the epoxide ring with formation of the corresponding amino alcohols which were converted into N-chloroacetyl derivatives. The latter underwent cyclization to N-Boc-protected 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones by the action of sodium hydride in DMF, and subsequent treatment with hydrogen chloride in ethyl acetate afforded 8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-one hydrochlorides.

Keywords

Morpholin Oxirane Maraviroc Sodium Hydride Tropane Alkaloid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • A. Yu. Mandzhulo
    • 1
    • 2
  • N. A. Mel’nichuk
    • 2
    • 3
  • V. N. Fetyukhin
    • 2
  • M. V. Vovk
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine
  2. 2.I.F. Lab Ltd.KievUkraine
  3. 3.Taras Shevchenko National University of KyivKievUkraine

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