Crystallographic evidence for the stereospecific synthesis of 4-amino-(D 3)-trishomocubanes: crystal structure of 3-methyl-(D 3)-trishomocubane-4-amine hydrochloride hydrate

Abstract

Abstract A series of C-3 substituted 4-amino-(D 3)-trishomocubanes with promising antiparkinsonian and antiviral activities has been recently synthesized via a modified Ritter reaction. The crystal structure of one of these compounds, the 3-methyl-(D 3)-trishomocubane-4-amine hydrochloride hydrate (C12H18N+Cl− · H2O) has been determined by X-ray diffraction. The symmetry is monoclinic, space group P21/c with a = 6.500(1) Å, b = 7.038(2) Å, c = 25.686(7) Å, β = 91.51(1)°, Z = 4. The 3S4S/3R4R stereochemistry is in favor of a one step rearrangement mechanism of the SN2 type for the synthesis of (D 3)-trishomocubanes via the Ritter reaction.