Next Article in Journal
Novel Penicillin-Type Analogues Bearing a Variable Substituted 2-Azetidinone Ring at Position 6: Synthesis and Biological Evaluation
Previous Article in Journal
Recent Advances in the Development and Application of Radiolabeled Kinase Inhibitors for PET Imaging
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(12), 22028-22043; doi:10.3390/molecules201219830

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
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 31 October 2015 / Revised: 24 November 2015 / Accepted: 2 December 2015 / Published: 10 December 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1986 KB, uploaded 10 December 2015]   |  

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. 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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top