Solvent-free optical resolution of N-methylamphetamine by distillation after partial diastereoisomeric salt formation

Chirality

Volumn 13, Issue 8, 2001, Pages 428-430

  Kozma, Dávid ^a   Fogassy, Elemér ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

2 Phenoxypropionic acid; 6 Methoxy methyl 2 naphthaleneacetic acid; Cis permetrinic acid; Diastereoisomeric salts; Distillation; O,O di p toluoyltartaric acid; O,O dibenzoyltartaric acid; Optical resolution; Solvent free process

Indexed keywords

METHAMPHETAMINE; NAPROXEN; PROPIONIC ACID DERIVATIVE; TARTARIC ACID;

CHIRALITY; CONFERENCE PAPER; CRYSTALLIZATION; DISTILLATION; DRUG STRUCTURE; OPTICS; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0034896424     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.1056     Document Type: Conference Paper

References (9)

1. Newman P. Optical resolution procedures for chemical compounds, vols. 1-3. New York: Optical Resolution Information Center, Manhattan College; 1978-84.
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3. Ács M, Bussche Ch, Seebach D. An efficient method of preparing (R)-and (S)-4,4,4-trifluoro-3-hydroxybutanoic acid: resolution with (R)- or (S)-1-phenylethylamine. Chimica 1990;44:90-92.
4. Ács M, Kozma D, Fogassy E. Enantiomer separation via diastereoisomeric salt formation by liquid-liquid phase transition. ACH Models Chem 1995;132:475-479.
5. Fogassy E, Ács M, Szili T, Simándi B, Sawinsky J. Molecular chiral recognition in supercritical solvents. Tetrahedron Lett 1994;35:257-260.
6. Ács M, Szili T, Fogassy E. New method of optical activation for racemic bases. Tetrahedron Lett 1991;32:7325-7328.
7. Fogassy E. Ács M, Faigl F, Simon K, Rohonczy J, Ecsery Z. Pseudosymmetry and chiral discrimination in optical resolution via diastereoisomeric salt formation. The crystal structures of (R)- and (S)-N-methylamphetamine bitartarates (RMERTA and SMERTA). J Chem Soc Perkin Trans 2 1986;1881-1886.
8. Kozma D, Madarász Z, Ács M, Fogassy E. Study of mechanism of an optical resolutions via diastereoisomeric salt formation by Pope-Peachy method. Tetrahedron Asym 1994;5:193.
9. The efficiency (0 < S < 1) of the optical resolution has been defined as the product of the optical purity (0 < OP < 1) and the yield (0 < Y < 1) of the precipitated salt: S = OPxY. Fogassy E, Lopata A, Faigl F, Darvas F, Ács M, Töke L. A quantitative approach to optical resolution. Tetrahedron Lett 1980;21:647-650.