Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

Jones, D. Heulyn and Bresciani, Stefano and Tellam, James P. and Wojno, Justyna and Cooper, Anthony W J and Kennedy, Alan R. and Tomkinson, Nicholas C O (2016) Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers. Organic and Biomolecular Chemistry, 14 (1). pp. 172-182. ISSN 1477-0520

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    Abstract

    The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.