Alkylation of tetrazoles using Mitsunobu conditions

Synthetic Communications

Volumn 26, Issue 14, 1996, Pages 2687-2694

  Purchase II, Claude F ^a   White, Andrew D ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029904389     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004585     Document Type: Article

References (16)

1. Reviews: a. Thornber, C. W. Chem. Soc. Revs. 1979, 8, 563. b. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Progress in Medicinal Chemistry 1980, 17, 151.
2. Reviews: a. Thornber, C. W. Chem. Soc. Revs. 1979, 8, 563. b. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Progress in Medicinal Chemistry 1980, 17, 151.
3. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem., 1994, 59, 234.
4. Reviews: a. Mitsunobu, O. Synthesis 1981, 1-28. b. Hughes, D. L. The Mitsunobu Reaction, in "Organic Reactions," Paquette, L. A. et al. Eds.; John Wiley & Sons, Inc.; New York, 1992, Vol. 42, 335-656.
5. Reviews: a. Mitsunobu, O. Synthesis 1981, 1-28. b. Hughes, D. L. The Mitsunobu Reaction, in "Organic Reactions," Paquette, L. A. et al. Eds.; John Wiley & Sons, Inc.; New York, 1992, Vol. 42, 335-656.
6. a. Bhagwat, S.; Gude, C. Tetrahedron Lett. 1994, 35, 1847.
7. b. Bonnal, C.; Chavis, C.; Lucas, M. J. Chem. Soc. Perkin Trans. 1 1994, 1401.
8. For a report on the alkylation of a tetrazolyl ring system using the Mitsunobu protocol, see Robert-Piessard, S.; Leblois, D.; Kumar, P; Robert, J. M.; Le Baut, G.; Sparfel, L.; Robert, B.; Khettab, E.; Sanchez, R. Y.; Petit, J. Y.; Welin, L. Eur. J. Med. Chem. 1990, 25, 737. For a report on the alkylation of tetrazoles with alcohols in the presence of zinc triflate, see Fortin, R.; Brochu, C. Tetrahedron Lett. 1994, 35, 9681.
9. For a report on the alkylation of a tetrazolyl ring system using the Mitsunobu protocol, see Robert-Piessard, S.; Leblois, D.; Kumar, P; Robert, J. M.; Le Baut, G.; Sparfel, L.; Robert, B.; Khettab, E.; Sanchez, R. Y.; Petit, J. Y.; Welin, L. Eur. J. Med. Chem. 1990, 25, 737. For a report on the alkylation of tetrazoles with alcohols in the presence of zinc triflate, see Fortin, R.; Brochu, C. Tetrahedron Lett. 1994, 35, 9681.
10. Purchase II, C. F.; White, A. D. U. S. Patent 5,362,744 1994.
11. The tetrazole 1 can be prepared as previously reported. See a. Finnegan, W. G.; Henry, R. A.; Lieber, E. J. Org. Chem. 1953, 18, 779. An improvement of one step has been reported. See b. Garbrecht, W. L.; Herbst, R. M. J. Org. Chem. 1953, 18, 1269.
12. The tetrazole 1 can be prepared as previously reported. See a. Finnegan, W. G.; Henry, R. A.; Lieber, E. J. Org. Chem. 1953, 18, 779. An improvement of one step has been reported. See b. Garbrecht, W. L.; Herbst, R. M. J. Org. Chem. 1953, 18, 1269.
13. 1,3 values for the cyclohexyl methine proton on the carbon bearing tetrazole (δ 5.42) are consistent with a syn relationship to the adjacent methine proton.
14. For a report on a new combination of reagents which results in higher yields of inverted esters from sterically hindered alcohols. See Tsunoda, T.; Yamamiya, Y.; Kawamura, Y.; Itô, S. Tetrahedron Lett. 1995, 36, 2529.
15. a. Herbst, R. M.; Wilson, K. R. J. Org. Chem. 1957, 22, 1142.
16. b. Garbrecht, W. L.; Herbst, R. M. J. Org. Chem. 1953, 18, 1003.