An efficient scalable route for the synthesis of enantiomerically pure tert -butyl-(1 R,4 S,6 R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

Organic Process Research and Development

Volumn 14, Issue 5, 2010, Pages 1239-1247

  Maton, William M ^a   Stazi, Federica ^a   Manzo, Angelo Maria ^a   Pachera, Roberta ^a   Ribecai, Arianna ^a   Stabile, Paolo ^a   Perboni, Alcide ^a   Giubellina, Nicola ^a   Bravo, Fernando ^a   Castoldi, Damiano ^a   Provera, Stefano ^a   Turco, Lucilla ^a   Bryant, Simon ^a   Westerduin, Pieter ^a   Profeta, Roberto ^a   Nalin, Arnaldo ^a   Miserazzi, Emanuele ^a   Spada, Simone ^a   Mingardi, Anna ^a   Mattioli, Mario ^a   Andreotti, Daniele ^a   more..

^a GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL TRANSFORMATIONS; DIASTEREOISOMERS; INNOVATIVE APPROACHES;

CARBOXYLATION; ENANTIOMERS; HEPTANE;

METHANOL;

EID: 77956938629     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op100164v     Document Type: Article

References (35)

1. Sakurai, T.; Amemiya, A.; Ishii, M.; Matsuzaki, I.; Chemelli, R. M.; Tanaka, H.; Williams, S. C.; Richardson, J. A.; Kozlowski, G. P.; Wilson, S.; Arch, J. R. S.; Buckingham, R. E.; Haynes, A. C.; Carr, S. A.; Annan, R. S.; McNulty, D. E.; Liu, W. S.; Terrett, J. A.; Elshourbagy, N. A.; Bergsma, D. J.; Yanagisawa, M. Cell 1998, 92, 573-585
2. Smart, D.; Jerman, J. C.; Brough, S. J.; Rushton, S. L.; Murdock, P. R.; Jewitt, F.; Elshourbagy, N. A.; Ellis, C. E.; Middlemiss, D. N.; Brown, F. Br. J. Pharmacol. 1999, 128, 1-3
3. Willie, J. T.; Chemelli, R. M.; Sinton, C. M.; Yanagisawa, M. Annu. Rev. Neurosci. 2001, 24, 429-458
4. Sakurai, T. Nat. Rev. Neurosci. 2007, 8, 171-181
5. Ohno, K.; Sakurai, T. Front. Neuroendocrinol. 2008, 29, 70-87
6. Chemelli, R. M.; Willie, J. T.; Sinton, C. M.; Elmquist, J. K.; Scammell, T.; Lee, C.; Richardson, J. A.; Williams, S. C.; Xiong, Y.; Kisanuki, Y.; Fitch, T. E.; Nakazato, M.; Hammer, R. E.; Saper, C. B.; Yanagisawa, M. Cell 1999, 98, 437-451
7. Lee, M. G.; Hassani, O. K.; Jones, B. E. J. Neurosci. 2005, 25, 6716-6720
8. Piper, D. C.; Upton, N.; Smith, M. I.; Hunter, A. J. Eur. J. Neurosci. 2000, 12, 726-730
9. Smart, D.; Jerman, J. C. Pharmacol. Ther. 2002, 94, 51-61
10. Smith, M. I.; Piper, D. C.; Duxon, M. S.; Upton, N. Neurosci. Lett. 2003, 341, 256-258
11. Amantini, D.; Alvaro, G.; Di Fabio, R.; Castiglioni, E.; Pavone, F. PCT/EP2009/066017, 2009.
12. For reviews on RCM, see
13. Samojowicz, C.; Bieniek, M.; Grela, K. Chem. Rev. 2009, 109, 3708-3742
14. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746-1787
15. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
16. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077
17. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388
18. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450
19. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041
20. Yang, Z.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621-8624
21. Chiral lactone 28 can be purchased from Minakem or Dr. Reddys. For the syntheses of 28 see
22. Sabbioni, G.; Jones, J. B. J. Org. Chem. 1987, 52, 4565-4570
23. Bolm, C.; Schiffers, I.; Dinter, C. L.; Gerlach, A. J. Org. Chem. 2000, 65, 6984-6991
24. Peschiulli, A.; Gunko, Y.; Connon, S. J. J. Org. Chem. 2008, 73, 2454-2457
25. Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763-5775
26. Kolb, M.; Barth, J. Synth. Commun. 1981, 11, 763-767
27. Kozhushkov, S. I.; Zlatopolskiy, B. D.; Brandl, M.; Alvermann, P.; Radzom, M.; Geers, B.; de Meijere, A.; Zeeck, A. Eur. J. Org. Chem. 2005, 854-863
28. ODonnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 19, 2641-2644
29. Yamada, S. I.; Oguri, T.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1976, 136-137
30. Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656-5682
31. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028
32. Marchand, P.; Lefèbvre, L.; Querniard, F.; Cardinaël, P.; Perez, G.; Counioux, J.-J.; Coquerel, G. Tetrahedron: Asymmetry 2004, 15, 2455-2465
33. A 72:28 mixture of tert -butyl ester 25 / 33 resulting from column chromatography and treated with trifluoroacetic acid afforded quantitatively the corresponding carboxylic acid 34 / 35 in a 72:28 ratio.
34. The analytical standards of 25 and 33 were obtained by column chromatography separation on silica gel (eluent: cyclohexane/ethyl acetate 7:3).
35. Ratio obtained in solution.