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Diasteroisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complimentary Methods for the Chiral Separation of cis/trans-Enantiomers of 3-Aminocyclohexanol

Brocklehurst, Cara and Laumen, Kurt and La Vecchia, Luigi and Shaw, Duncan and Voegtle, Markus (2011) Diasteroisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complimentary Methods for the Chiral Separation of cis/trans-Enantiomers of 3-Aminocyclohexanol. Organic Process Research and Development, 15 (1). pp. 294-300. ISSN 1083-6160

Abstract

The paper demonstrates the prep scale synthesis of (1S,3S)-3-aminocyclohexanol via either enzymatic kinetic resolution of Cbz-protected 3-aminocyclohexanols, or via direct diasteroisomeric salt formation with (R)-mandelic acid. The salt formation demonstrates how a single enantiomer, (1S,3S)-3-aminocyclohexanol (R)-mandelate, can be effectively isolated from the cis/trans racemic mixture and subsequently converted to the free amine, (1S,3S)-3-aminocyclohexanol, by ion-exchange chromatography. We have also demonstrated how the other three enantiomers of 3-aminocyclohexanol could be prepared by either diasteroisomeric salt formation or enzymatic kinetic resolution.

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Date Deposited: 13 Oct 2015 13:16
Last Modified: 13 Oct 2015 13:16
URI: https://oak.novartis.com/id/eprint/3395

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