Upscaling the solid-phase synthesis of a tetrahydrocarbazole in chemical development

Organic Process Research and Development

Volumn 10, Issue 3, 2006, Pages 441-445

  Prühs, Stefan ^a   Dinter, Christian ^a   Blume, Thorsten ^a   Schütz, Armin ^a   Harre, Michael ^a   Neh, Harribert ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745752185     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0502607     Document Type: Article

References (24)

1. Koppitz, M.; Reinhardt, G.; van Lingen, A. Tetrahedron Lett. 2005, 46, 911-914.
2. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-601.
3. (b) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
4. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J. Tetrahedron 1996, 52, 4527-4554.
5. (a) Raillard, S.; Ji, G.; Mann, A. D.; Baer, T. A. Org. Process Res. Dev. 1999, 3, 177-183.
6. (b) Meisenbach, M.; Allmendinger, T.; Mak, C.-P. Org. Process Res. Dev. 2003, 7, 553-558.
7. (a) Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
8. (b) Bernatowicz, M. S.; Daniels, S. B.; Köster, H. Tetrahedron Lett. 1989, 30, 4645-4648.
9. (c) Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730-3743.
10. (a) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-1430.
11. (b) Kolodzicj, S. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277-5280.
12. (c) Kaldor, S. W.; Fritz, J. E.; Tang, J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041-3044.
13. (d) Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockermann, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874-4881.
14. (a) Albericio, F.; Barany, G. Int. J. Peptide Prot. Res. 1987, 30, 206-216.
15. (b) Fivush, A. M.; Willson, T. M. Tetrahedron Lett. 1997, 38, 7151-7154.
16. (c) Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. A. J. Org. Chem. 1997, 62, 1240-1256.
17. Penke, B.; Rivier, J. J. Org. Chem. 1987, 52, 1197-1200.
18. Britten, A.; Lockwod, G. J. Chem. Soc., Perkin Trans. 1974, 1, 1824-1827.
19. Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869-4872.
20. Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706-3716.
21. Zikos, C. C.; Frederigos, N. G. Tetrahedron Lett. 1995, 36, 3741-3744.
22. A repetitive execution of the small-scale research synthesis is not practical due to large amounts of needed building bock 3.
23. Only material costs are considered for total costs of the product.
24. Kortenaar, P. B. W.; Van Dijk, B. G.; Peeters, J. M.; Raaben, B. J.; Hans. P. J.; Adams, M.; Tesser, G. I. Int. J. Peptide Prot. Res. 1986, 27, 398-400.