Stereoselective crystallization of 3-(2,6-dimethylphenoxy)propane-1,2-diol: preparation of the single-enantiomer drug mexiletine

Add time:07/11/2019    Source:sciencedirect.com

Racemic 3-(2,6-dimethylphenoxy)propane-1,2-diol 8 undergoes spontaneous resolution upon crystallization. This fact is confirmed by the melting point inspection, vibration spectra and X-ray single crystal diffraction of racemic and scalemic crystalline samples of 8. Racemic 8 has been effectively resolved by a preferential crystallization procedure into (S)- and (R)-enantiomers with ee of approximately 90%. The enantiomeric purity of (S)- and (R)-8 could be increased to ee >99% through simple recrystallization. Nonracemic diols 8 were converted into nonracemic 1,2-epoxy-3-(2,6-dimethylphenoxy)propanes (S)- and (R)-7 with ee 98% via Mitsunobu reaction. The reaction proceeded without loss of enantiomeric purity, and the initial configuration of the stereogenic center was conserved. Enantiopure epoxides 7 were converted into nonracemic 1-(2,6-dimethylphenoxy)propan-2-ols 2, which are valuable intermediates in single-enantiomer mexiletine synthesis.

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