1. Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen
- Author
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Mario Ordóñez, Iris J. Montoya-Balbás, Berenice Valentín-Guevara, Irma Linzaga-Elizalde, Perla Román-Bravo, and Estefanía López-Mendoza
- Subjects
Naproxen ,(S)-naproxen ,Lactams ,Decarboxylation ,Hydrochloride ,baclofen ,Pharmaceutical Science ,Medicinal chemistry ,Article ,Catalysis ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Michael addition ,Drug Discovery ,medicine ,Organic chemistry ,Physical and Theoretical Chemistry ,Nitromethane ,Chemistry ,Aryl ,Organic Chemistry ,resolution ,Stereoisomerism ,β-aryl-γ-lactams ,phenibut ,Raney nickel ,Chemistry (miscellaneous) ,Michael reaction ,Molecular Medicine ,Saponification ,medicine.drug - Abstract
An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-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.
- Published
- 2015
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