Resolution of 1-cyclohexylethylamine via diastereomeric salt formation with enantiopure 2-phenylacetic acids

Tetrahedron Asymmetry

Volumn 17, Issue 10, 2006, Pages 1541-1543

  Sakai, Kenichi ^a   Yokoyama, Masami ^a   Sakurai, Rumiko ^a   Hirayama, Noriaki ^b  

^a Yamakawa Chemical Industry Co Ltd   (Japan)

^b TOKAI UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 CYCLOHEXYLETHYLAMINE; 2 METHOXY 2 PHENYLACETIC ACID; ETHYLAMINE; HYDRATROPIC ACID; PHENYLACETIC ACID DERIVATIVE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL;

EID: 33745400133     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.010     Document Type: Article

References (16)

1. Jacques J., Collet A., and Wilen S.H. Enantiomers, Racemates, and Resolutions (1981), Wiley-InterScience
2. Kozma D. Optical Resolutions via Diastereomeric Salt Formation (2002), CRC Press
3. Nohira H., and Sakai K. Optical Resolution by Means of Crystallization. In: Toda F. (Ed). Enantiomer Separation: Fundamental and Practical Method, January (2005), Kluwer Academic Publishers, Netherlands 165-191
4. Rouhi A.M. Chemical and Engineering News (2003) 45-55
5. (SRC kinase inhibotor): Armstrong, H. M. et al., USP 6,498,165, 2002.
6. (Fused pyridine inhibitor): Macor, J. E., USP 6,326,379, 2001.
7. (IMPDH enzyme Inhibotor): Iwanowicz, E. J.; Dhar, M.; Leftheris, K.; Liu, C.; Mitt, T.; Watterson, S. H.; Barrish, J. C., USP 6,420,403, 2002.
8. Sunjic, V.; Kontrec, D.; Vincovic, V., USP 6,437,147, 2002.
9. Yamada, S.; Seki, M.; Yoshioka, R. Shibatani, T.; Japan Patent Kokai 1999-322668.
10. Seki M., Yamada S., Kuroda T., Imashiro R., and Shimizu T. Synthesis (2000) 1677
11. 2):. Freifelder M., and Stone G.R. J. Am. Chem. Soc. 80 (1958) 5270-5272
12. 2):. Leithe W. Chem. Ber. 65 (1932) 660-666
13. 2):. Kornblum N., Gurowitz W.D., Larson H.O., and Hardies D.E. J. Am. Chem. Soc. 82 (1960) 3099-3102
14. (Pt/C):. Reihlen H., Knopfle L., and Sapper W. Liebigs Ann. Chem. 534 (1938) 247
15. Hoback, K. F., Ph.D. thesis, University of West Virginia, 1955.
16. De % is based on the enantiomeric excess (ee) of amine 1 liberated from the less-soluble salt. The yield is calculated based on (RS)-1. Resolution efficiency (E, %) = Yield (%) × De (%) × 2/100.