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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 20
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Original Articles

Efficient One-Pot Synthesis of the GABAB Positive Allosteric Modulator (R,S)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one

, , , , &
Pages 3398-3405 | Received 15 Jan 2008, Published online: 30 Sep 2008
 

Abstract

The GABAB positive allosteric modulator (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (1) was synthesized in one pot from the anhydrous lithium salt of 2,4-di-tert-butylphenol and methyl trifluoropyruvate mediated by a stoichiometric amount of anhydrous gallium(III) chloride in 64% overall yield. The enantiomers of 1 were separated by chiral-phase HPLC (Chiralpak AD®), and the absolute configuration was determined by X-ray crystallography.

ACKNOWLEDGMENTS

We thank Daniel Zimmerli for separation of the enantiomers of 1 and the analytical department PRBD-E for measuring and interpreting 1HNMR and MS spectra.

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