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

Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico
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Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(12), 22028-22043; https://doi.org/10.3390/molecules201219830
Received: 31 October 2015 / Revised: 24 November 2015 / Accepted: 2 December 2015 / Published: 10 December 2015
(This article belongs to the Section Organic Chemistry)
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. View Full-Text
Keywords: β-aryl-γ-lactams; Michael addition; resolution; (S)-naproxen; baclofen; phenibut β-aryl-γ-lactams; Michael addition; resolution; (S)-naproxen; baclofen; phenibut
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Montoya-Balbás, I.J.; Valentín-Guevara, B.; López-Mendoza, E.; Linzaga-Elizalde, I.; Ordoñez, M.; Román-Bravo, P. Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen. Molecules 2015, 20, 22028-22043.

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