Utilizing capillary gas chromatography mass spectrometry to determine 4-benzotrifluoride t-butyl ether as a reaction by-product in fluoxetine synthesized using potassium t-butoxide as base

Journal of Pharmaceutical and Biomedical Analysis

Volumn 31, Issue 1, 2003, Pages 63-74

  Robbins, David K ^a   Dodson, Paul N ^a   Buccilli, Lynne A ^a   Mitchell, David ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

4 Benzotrifluoride t butyl ether; Fluoxetine; Gas chromatography; Mass spectrometry; Potassium t butoxide

Indexed keywords

4 BENZOTRIFLUORIDE TERT BUTYL ETHER; ETHER DERIVATIVE; FLUOXETINE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; SODIUM DERIVATIVE; SODIUM HYDRIDE; TRACE ELEMENT; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; DRUG DETERMINATION; DRUG SCREENING; DRUG SYNTHESIS; ION MONITORING; LINEAR SYSTEM; MASS SPECTROMETRY; PRIORITY JOURNAL; SPIKE WAVE; TABLET MATRIX;

BUTANOLS; FLUOROBENZENES; FLUOXETINE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; PHENYL ETHERS; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; SOLVENTS;

EID: 0037419727     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0731-7085(02)00605-2     Document Type: Article

References (22)

1. Fuller R.W., Wong D.T., Robertson D.W. Med. Res. Rev. 11-1:1991;17-34.
2. Benfield P., Heel R.C., Lewis S.P. Drugs. 32:(6):1986;481-508.
3. Stark P., Hardison C.D. J. Clin. Psychiatry. 46:1985;53-58.
4. Zerbe R.L., Rowe H., Enas G.G., Wong D., Faried N., Lemberger L. J. Pharmacol. Exp. Ther. 232:1985;139-143.
5. Wong D.T., Bymaster F.P. Res. Commun. Chem. Pathal. Pharmacol. 15:1976;221-231.
6. B.B. Molloy, K.K. Schmiegel, US Patent 4,314,081, 1982.
7. P.J. Kairisalo, P.J. Hukka, A.H. Jarvinen, US Patent 5,166,437, 1992.
8. Kumar A., Ner H.D., Dike S.Y. Tetrahedron Lett. 32:1991;1901-1904.
9. Gao Y., Sharpless K.B. J. Org. Chem. 53:1988;4081-4084.
10. Srebnik M., Ramachandran P.V., Brown H.C. J. Org. Chem. 53:1988;2916-2920.
11. Corey E.J., Riechard G.A. Tetrahedron Lett. 30:1989;5207-5210.
12. Bottini A.T., Corson F.P., Fitzgerald R., Frost K.A. Tetrahedron. 28:(18):1972;4883-4904.
13. Bottini A.T., Corson F.P., Fitzgerald R., Frost K.A. Tetrahedron Lett. 54:1970;4753-4756.
14. DiBlase S.A., Gokel G.W. J. Org. Chem. 43:1978;447-452.
15. Hales R.H., Bradshaw J.S., Pratt D.R. J. Org. Chem. 36:1971;314-318.
16. Bradshaw J.S., Hales R.H. J. Org. Chem. 36:1971;318-322.
17. Gokel G.W., Cram D.J., Liotta C.L., Harris H.P., Cook F.L. J. Org. Chem. 39:1974;2445-2446.
18. Paquette L.A., Houser R.W. J. Org. Chem. 36:1971;1015-1016.
19. Pearson D.E., Buehler C.A. Chem. Rev. 74:1974;45-86.
20. Wirth D.D., Miller M.S., Boini S.K., Koenig T.M. Org. Process Res. Dev. 4:(6):2000;513-519.
21. Wirth D.D., Olsen B.A., Hallenbeck D.K., Lake M.E., Gregg S.M., Perry F.M. Chromatographia. 46:1997;511-513.
22. 3, 300 MHz) d 7.52, (d, J=8.50 Hz, 2 H), 7.04 (d, J=8.58 Hz, 2 H), 1.38 (s, 9 H).