Development of a preparative-scale asymmetric synthesis of (R)-p-tolyl methyl sulfoxide for use in a one-pot synthesis of a drug intermediate containing a trifluoromethyl-substituted alcohol functionality

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 605-608

  Han, Zhengxu ^a   Song, Jinhua J ^a   Yee, Nathan K ^a   Xu, Yibo ^a   Tang, Wenjun ^a   Reeves, Jonathan T ^a   Tan, Zhulin ^a   Wang, Xiao Jun ^a   Lu, Bruce ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

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EID: 39049136533     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700010a     Document Type: Article

References (12)

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2. (a) Pedrosa, R.; Sayalero, S.; Vicente, M.; Maestro, A. J. Org. Chem. 2006, 71, 2177-2180 and references therein.
3. (b) Fujisawa, T.; Takemura, I.; Ukaji, Y. Tetrahedron Lett. 1990, 31, 5479-5482.
4. Carreno, M. C. Chem. Rev. 1995, 85, 1717-1760.
5. Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651-3705.
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7. Bravo, P.; Bruche, L.; Farina, A.; Gerus, I. I.; Kolytcheva, M. T.; Kukhar, V.; Meille, S. V.; Viani, F. J. Chem. Soc., Perkin Trans. 1 1995, 1667-1671.
8. Izzo, I.; Crumble, R.; Solladie, G.; Hanquet, G. Tetrahedron: Asymmetry 2005, 16, 1503-1511.
9. Han, Z.; Krishnamurthy, D.; Grover, P. Fang, Q. K.; Su, X.; Willcinson, H. S.; Lu, Z.; Magiera, D.; Senanayake, C. H. Tetrahedron 2005, 61, 6386-6408 and references therein.
10. See the Experimental Section for the chiral HPLC method.
11. f values are as follows: desired alcohol (major isomer): 0.56; minor isomer: 0.37; N-tosyl norephedrine: 0.32; sulfoxide: 0.08.
12. See Experimental Section for details.