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Issue 9, 2010
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Regio- and diastereoselective ring-opening of (S)-(−)-2-(trifluoromethyl)oxirane with chiral 2,5-disubstituted tetrahydroquinolines in hexafluoro-2-propanol

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Abstract

Multi-hundred grams of (S)-1,1,1-trifluoro-3-{(R)-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-3,4-dihydroquinolin-1(2H)-yl}propan-2-ol, a potent cholesteryl ester transfer protein (CETP) inhibitor, was prepared in quantitative isolated yield (>99%) with excellent chemical (>99% HPLC area%) and optical (>99% de) purities. The cornerstone to these results were achieved by regiospecific and diastereoselective ring-opening of optically pure (S)-(−)-2-(trifluoromethyl)oxirane (>99% ee) with (R)-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydroquinoline (>99% ee) in hexafluoro-2-propanol at 22 °C for 24 h. This reaction did not require a rare earth metal salt (Yb(OTf)3) as the catalyst nor a column chromatography for the purification. The excess (S)-(−)-2-(trifluoromethyl)oxirane and the solvent hexafluoro-2-propanol were recovered by distillation from the reaction and reused.

Graphical abstract: Regio- and diastereoselective ring-opening of (S)-(−)-2-(trifluoromethyl)oxirane with chiral 2,5-disubstituted tetrahydroquinolines in hexafluoro-2-propanol

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Article information


Submitted
29 Mar 2010
Accepted
01 Jul 2010
First published
30 Jul 2010

Green Chem., 2010,12, 1548-1551
Article type
Communication

Regio- and diastereoselective ring-opening of (S)-(−)-2-(trifluoromethyl)oxirane with chiral 2,5-disubstituted tetrahydroquinolines in hexafluoro-2-propanol

X. Li, R. K. Russell, H. Chen, Y. Zhang, S. Ballentine, J. Spink, S. Branum, F. Liu, Y. Chen, T. Rammeloo, W. Aelterman, K. L. Sorgi and W. V. Murray, Green Chem., 2010, 12, 1548
DOI: 10.1039/C004726K

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