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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 (C 12 H 18 N + Cl −  · H 2 O) has been determined by X-ray diffraction. The symmetry is monoclinic, space group  P 2 1 / c  with  a  = 6.500(1) Å,  b  = 7.038(2) Å,  c  = 25.686(7) Å,  β  = 91.51(1)°,  Z  = 4. The 3 S 4 S /3 R 4 R  stereochemistry is in favor of a one step rearrangement mechanism of the SN 2  type for the synthesis of ( D  3 )-trishomocubanes via the Ritter reaction.

zeitschrift für kristallographie - crystalline materials

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