(Z,1S,10aR)-()-Menthyl 1-hydroxy- 1,2,3,5,6,7,10,10a-octahydropyrrolo- [1,2-a]azocine-10a-carboxylate

The structure determination confirms the stereochemistry of the title compound, C21H35NO3, obtained as an intermediate in the enantioselective synthesis of deoxynojirimicine analogs. The system contains a pyrrolo[1,2-a]azocine backbone, which was synthesized by a domino process involving a [2,3]-sigmatropic rearrangement. The incorporation of a chiral auxiliary ()-menthyl, whose stereocentres are not involved during the synthesis, enables the assignation of absolute configuration. The crystal structure features O--H O hydrogen bonds involving the hydroxy groups as donors and the carbonyl groups as acceptors, which link the molecules into chains running along [010].