(1S,2R,4S)-1-[(Benzylamino)methyl]-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

The title compound, C17H25NO2, was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclohexenylmethanol], followed by the oxirane ring-opening by benzylamine using [Ca(CF3CO2)(2)] as catalyst under solvent-free condition at 313 K. The molecular conformation is stabilized by an intramolecular O-H center dot center dot center dot N hydrogen bond. In the crystal, molecules are linked by intermolecular N-H center dot center dot center dot O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O-H center dot center dot center dot O hydrogen bonds into sheets parallel to (010). The absolute configuration of the molecule is known from the synthetic procedure.