Chemistry of Heterocyclic Compounds

, Volume 15, Issue 4, pp 409–412 | Cite as

Conformational analysis and stereochemistry of the reduction of 2-alkoxymethyl-4-oxopiperidines

  • R. S. Vartanyan
  • É. A. Mistryukov


The isomer with an axially oriented alkoxymethyl group predominates in the equilibrium mixture of 1-aklyl-2,5-dimethyl-2-alkoxymethyl-4-piperidones investigated under both alkaline and acidic equilibrium conditions, and its percentage increases as the volume of the alkoxy group increases in the order Me, Et, iso-Pr. The reduction of 4-ketopiperidines that contain a polar function in the 2 position follows the same principles as those that obtain when it is absent, i.e., exclusively the equatorial alcohols are obtained in the case of reduction with lithium and ethanol in liquid ammonia, whereas primarily the axial alcohols are obtained in the case of reduction with sodium borohydride. The selectivity of the reduction increases on passing from the free bases to the hydrochlorides.


Alcohol Ammonia Lithium Hydrochloride Equilibrium Condition 
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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • R. S. Vartanyan
    • 1
  • É. A. Mistryukov
    • 1
  1. 1.A. L. Mndzhoyan Institute of Fine Organic ChemistryAcademy of Sciences of the Armenian SSRYerevan

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