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

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

Iris J Montoya-Balbás, Berenice Valentín-Guevara, Estefanía López-Mendoza, Irma Linzaga-Elizalde, Mario Ordoñez, Perla Román-Bravo

Molecules. 2015 Dec 10;20(12):22028-43.

PMID: 26690390

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP63701564	S(−)-Baclofen hydrochloride		63701-56-4	Price

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