Synthesis, resolution and absolute configuration of a tolperisone metabolite

J. Bálint, Imre Markovits, G. Egri, Zsuzsanna Tuza, L. Párkányí, E. Fogassy

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

1-(4′-Hydroxymethyl-phenyl)-2-methyl-3-(piperidine-1-yl)-propane-1-one M2, a metabolite of tolperisone, was synthesised in a solvent-free Mannich reaction. The optical resolution was carried out by diastereoisomeric salt formation and separation, for which three resolving agents ((2R,3R)-O,O′-dibenzoyl tartaric acid, (2R,3R)-O,O′-di-p-toluoyl tartaric acid and (R)-2-hydroxy-4-(2-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaphosphorinane-2- oxide (anicyphos)) were found. The absolute configuration of M2 was determined by the single-crystal X-ray diffraction method.

Original languageEnglish
Pages (from-to)719-724
Number of pages6
JournalTetrahedron Asymmetry
Volume12
Issue number5
DOIs
Publication statusPublished - Apr 2 2001

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Tolperisone
metabolites
Metabolites
Propane
acids
piperidine
Acids
synthesis
configurations
X-Ray Diffraction
propane
Salts
Single crystals
salts
X ray diffraction
Oxides
oxides
single crystals
diffraction
x rays

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis, resolution and absolute configuration of a tolperisone metabolite. / Bálint, J.; Markovits, Imre; Egri, G.; Tuza, Zsuzsanna; Párkányí, L.; Fogassy, E.

In: Tetrahedron Asymmetry, Vol. 12, No. 5, 02.04.2001, p. 719-724.

Research output: Contribution to journalArticle

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