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- Title
Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)-and (S)-Baclofen.
- Authors
Montoya-Balbás, Iris J.; Valentín-Guevara, Berenice; López-Mendoza, Estefanía; Linzaga-Elizalde, Irma; Ordoñez, Mario; Román-Bravo, Perla
- 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.
- Subjects
CHEMICAL synthesis; LACTAMS; AROMATIC compound synthesis; NAPROXEN; BACLOFEN; NITROMETHANE; DECARBOXYLATION
- Publication
Molecules, 2015, Vol 20, Issue 12, p22028
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules201219830