Enantiomeric enrichment of (+)-(3R,4S)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine by crystallization

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Authors	NAVRÁTILOVÁ Hana POTÁČEK Milan
Year of publication	2001
Type	Article in Periodical
Magazine / Source	Enantiomer
MU Faculty or unit	Faculty of Science
Citation
Field	Organic chemistry
Keywords	enantiomeric enrichment; paroxetine; piperidines; crystalization;
Description	Two-fold crystallization of 4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl- piperidine enriched in (+)-enantiomer 3b (65.2-79.4%ee) yielded the racemate that crystallized out of solution and the mother liquor highly enriched in 3b (95.4-97.6% ee). Differences in infrared spectra of the racemate and enantiomer proved that the racemate consists of a racemic compound. Furthermore, solution NMR spectra of enriched 3b showed differentiation of some resonances (self-induced non-equivalence) which indicated strong diastereomeric interactions between solutes in apolar solvent. The enantiomeric composition of products was determined by NMR spectroscopy in the presence of R-Mosher acid.
Related projects:	Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles