(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].