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Enantiomeric analysis of (3S,4R)-4-(4-fluorophenyl)- 3-hydroxymethyl-1-methylpiperidine by 19F NMR spectroscopy

✍ Scribed by Hana Navrátilová

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 134 KB
Volume: 39
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.940

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✦ Synopsis

Abstract

The chemical‐shift anisochrony Δδ of the fluorine signal for the enantiomerically enriched (3__S__,4__R__)‐4‐(4‐fluorophenyl)‐3‐hydroxymethyl‐1‐methylpiperidine (1a) was induced in the presence of S‐Mosher acid (2) and its magnitude varied with the enantiomeric purity of 1a. Very low quantities of an enantiomeric impurity (1b), ranging typically from 0.2 to 1%, were evaluated by comparing peak areas of 1b with those of ^13^C satellite signals that were deconvoluted using an automatic Lorentzian line fitting. Isotopic shifts and ^13^C^19^F coupling constants were extracted from the corresponding fluorine and carbon spectra. Copyright © 2001 John Wiley & Sons, Ltd.

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