Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1125-1128

  Hett, Robert ^a   Fang, Qun Kevin ^a   Gao, Yun ^a   Hong, Yaping ^a   Butler, Hal T ^a   Nie, Xiaoyi ^a   Wald, Stephen A ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMOTEROL;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031575631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00088-9     Document Type: Article

References (25)

1. 1. (a) Anderson, G. P. in "New Drugs in Allergy and Asthma", Birkhäuser Verlag, Basel, 1993.
2. (b) Anderson, G. P. Life Sciences 1993, 52, 2145.
3. 2. (a) Waldeck, B. Chirality 1993, 5, 350.
4. (b) Millership, J. S.; Fitzpatrick, A. Chirality 1993, 5, 573.
5. (c) Testa, B; Trayer, W. F. Chrality 1990, 2, 129.
6. (d) Ariens, E. J. Schweiz. Med Wschr. 1990, 120 (5), 131
7. 3. (a) Murase, K.; Mase, T.; Ida, H.; Takahashi, K.; Murakami, M. Chem. Pharm. Bull. 1978, 26, 1123;
8. (b) Trofast, J.; Österberg, K.; Källström, B.-L.; Waldeck, B. Chirality 1991, 3, 443.
9. 4. The synthesis of the racemic epoxide and the bromketone is described in: Kaiser, C.; Colella, D. F.; Schwartz, M. S.; Garvey, E.; Wardel, Jr. J. R. J. Med. Chem. 1974, 17, 49.
10. 5. (a) Hong, Y.; Gao, Y.; Nie, X, Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631.
11. (b) Hong, Y.; Gao, Y.; Nie, X, Zepp, C. M. Tetrahedron Lett. 1994, 35, 5551.
12. (c) Di Simone, B.; Savoia, D; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1995, 6, 301
13. 6. The asymmetric synthesis of optically pure cis-1-amino-2-indanols will be addressed in a separate paper. Also see: Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W., Larsen, R. D.; Verhoven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993.
14. 7. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Carrol, J. D.; Corley, E. G.; Grabowski, E. J. J. Org,. Chem. 1993, 58, 2880.
15. 8. Chiracel OJ, 10 μm, 25 cm × 4.6 mm (Daicel); mobile phase hexane/ ethanol = 7/3, ambient temperature, flow rate 1.0 ml/min, retention times (R) = 21 min, (S) = 23.5 min.
16. 9. (a) Corey, E. J.; Bakshi, R. K.; Shibita, S. J. J. Am. Chem. Soc. 1987, 109, 5551.
17. (b) Corey, E. J.; Bakshi, R. K.; Shibita, S. J.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
18. (c) Corey, E. J.; Shibita, S. J. ; Bakshi, R. K.J. Org Chem. 1988, 53, 2861.
19. 3) ee = 96%.
20. 11. In the USA 4-Methoxyamphetamine is a schedule 1 controlled substance DEA 7411.
21. 12. M. Freifelder in "Practical Catalytic Hydrogenation", Wiley-Interscience, New York, 1970.
22. 13. (a) Murase, K.; Mase, T.; Ida, H.; Takahashi, K.; Murakami, M. Chem. Pharm. Bull. 1977, 25, 1368;
23. (b) Trofast, J. W.; Jakupovic, E.; Månsson, L. K.; PCT Int. Appl. WO 92/05147.
24. 14. While the (R,S) and (S,R) diastereomers of the free base are crystalline solids (see ref 3a), the (R,R) and (S,S) diastereomers are amorphous solids and could not be crystallized without salt formation.
25. 2NH = 85 / 15 / 0.1, ambient temperature, flow rate 1.0 ml/min, retention times (R,R) = 17.0 min, (R,S) = 19.2 min, (S,R) = 23.6, (S,S) = 26.8 min.