Optical resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline by supercritical fluid extraction

6‐Fluoro‐2‐methyl‐1,2,3,4‐tetrahydroquinoline (FTHQ) enantiomers were separated by supercritical fluid extraction using carbon dioxide. Diastereoisomeric salts were formed from the racemic base with less than one equivalent of O,O′‐di‐(4‐toluoyl)‐(2R,3R)‐tartaric acid (DPTTA). Further purification w...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2001, Vol.13 (9), p.568-570
Main Authors: Kmecz, Ildikó, Simándi, Béla, Bálint, József, Székely, Edit, Fogassy, Elemér, Kemény, Sándor
Format: Article
Language:English
Subjects:
4-tetrahydroquinoline
6-fluoro-2-methyl-1
6‐fluoro‐2‐methyl‐1,2,3,4‐tetrahydroquinoline
Anti-Infective Agents - isolation & purification
carbon dioxide
Carbon Dioxide - chemistry
chiral resolution
diastereoisomeric salt formation
enantiomer
Indicators and Reagents
optical resolution
Quinolines - isolation & purification
Stereoisomerism
supercritical fluid extraction (SFE)
Temperature
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Summary:6‐Fluoro‐2‐methyl‐1,2,3,4‐tetrahydroquinoline (FTHQ) enantiomers were separated by supercritical fluid extraction using carbon dioxide. Diastereoisomeric salts were formed from the racemic base with less than one equivalent of O,O′‐di‐(4‐toluoyl)‐(2R,3R)‐tartaric acid (DPTTA). Further purification was achieved by partial salt formation of the enantiomeric mixture with an achiral acid (HCl) followed by the supercritical fluid extraction of the free enantiomers. Chirality 13:568–570, 2001. © 2001 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.1178