RESUMO

An efficient synthesis of enantiomerically-pure ß-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of ß-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

Assuntos

Baclofeno/síntese química , Lactamas/síntese química , Naproxeno/química , Catálise , Estereoisomerismo

RESUMO

In the title compound, C(14)H(10)N(2)O(2), the phtalimide and 2-pyridylmethyl units are almost perpendicular, with an inter-planar angle of 85.74 (2)°. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming chains running along the b axis. The packing is further stabilized by offset π-π inter-actions between adjacent pyridine rings, with a centroid-centroid distance of 3.855 (2) Å.