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Efficient Synthesis of ?-Aryl-?-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen.

ABSTRACT: An efficient synthesis of enantiomerically-pure ?-aryl-?-lactams is described. The principal feature of this synthesis is the practical resolution of ?-aryl-?-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 ?-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.

SUBMITTER: Montoya-Balbas IJ

PROVIDER: S-EPMC6332160 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen.

Montoya-Balbás Iris J IJ Valentín-Guevara Berenice B López-Mendoza Estefanía E Linzaga-Elizalde Irma I Ordoñez Mario M Román-Bravo Perla P

Molecules (Basel, Switzerland) 20151210 12

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 prepar ...[more]

PMID: 26690390

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