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Synthesis 1991; 1991(1): 43-46
DOI: 10.1055/s-1991-26376
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trans-2-Cyanocycloalkanols: Versatile Synthons for Alicyclic cis- and trans-1,3-Amino Alcohols

Ferenc Fülöp* , Imre Huber, Gábor Bernáth, Helmut Hönig, Peter Seufer-Wasserthal
  • *Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, POB 121, H-6701 Szeged, Hungary
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Publication Date:
17 September 2002 (online)

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From trans-2-hydroxycyclopentanecarbonitrile (1) and trans-2-hydroxycyclohexanecarbonitrile (2), a number of trans-2-aminomethylcycloalkanols are prepared by reductive alkylation. Inversion of trans-N-acylaminocycloalkanols by treatment with thionyl chloride and subsequent hydrolysis gives the cis counterparts. The enantiomerically pure trans-2-aminomethylcyclohexanols 13 and 14 are also prepared.