Enantiospecific synthesis of rpr 107880 : A new non peptide substance P antagonist

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3125-3128

  Mutti, Stéphane ^a   Daubié, Christophe ^a   Decalogne, François ^a   Fournier, Robert ^a   Rossi, Pierre ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 METHOXYPHENYL) 2 [2 (2 METHOXYPHENYL) PROPIONYL] 6 METHYLPERHYDROISOINDOL 4 OL; ISOINDOLE DERIVATIVE; SUBSTANCE P ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030003856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00519-9     Document Type: Article

References (21)

1. Tabart, M.; Peyronel, J.F. Bioorga. Med Chem. Lett. 1994, 4, 673-676.
2. Rhône-Poulenc Rorer Patent WO 9504040.
3. (a) Oppolzer, W. ; Petrzilka, M. Helv. Chem. Acta 1978, 61, 2755-2762. (b) Caine, D. ; Procter, K. ; Cassell, R.A. J. Org. Chem. 1984, 49, 2647-2648. Nangia, A. ; Prasuna, G. Synth. Comm. 1994, 24, 1899-1998.
4. (a) Oppolzer, W. ; Petrzilka, M. Helv. Chem. Acta 1978, 61, 2755-2762. (b) Caine, D. ; Procter, K. ; Cassell, R.A. J. Org. Chem. 1984, 49, 2647-2648. Nangia, A. ; Prasuna, G. Synth. Comm. 1994, 24, 1899-1998.
5. (a) Oppolzer, W. ; Petrzilka, M. Helv. Chem. Acta 1978, 61, 2755-2762. (b) Caine, D. ; Procter, K. ; Cassell, R.A. J. Org. Chem. 1984, 49, 2647-2648. Nangia, A. ; Prasuna, G. Synth. Comm. 1994, 24, 1899-1998.
6. Determined by GC analysis.
7. Reusch, W.; Johnson, C.K. J. Org. Chem. 1963, 28, 2557-2560.
8. Yamamoto, K. ; Yamamoto, N. Chem. Lett. 1989, 1149-1152.
9. The trans-isomer can be efficiently purified by crystallization in pentane in 30% yield.
10. Determined by HPLC analysis.
11. Mc Killop, A. ; Tarbin, J.A. Tetrahedron Lett. 1983, 24, 1505-1508.
12. Trost, B.M.; Salzmann, T.N. ; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887-4902.
13. The enantiomeric purity was determined by GC using a chiral phase. This work has been performed by D. Lurier and G. Ducrotoy (Rhône-Poulenc Rorer).
14. Hosomi, A., Sakata, Y. ; Sakurai, H. Chem. Lett. 1984, 1117-1120.
15. Terao, Y. ; Kotaki, H. ; Imai, N. ; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896-898.
16. Fray, A.H. ; Meyers, A.I. Tetrahedron Lett. 1992, 33, 3575-3578.
17. o-Anisyllithium was prepared by orthometallation of anisole by nBuli in THF at O°C.
18. LiBr salts were added to reduce enolization and to improve chemical yield.
19. 2 : C78.6, H8.32, N3.98, O9.1, found : C78.3, H8.7, N4.1, O8.9.
20. Mutti, S. ; Daubié, C. ; Decalogne, F. ; Fournier, R. ; Montuori, O. ; Rossi, P. Synth. Comm., in press.
21. 4 : C73.73, H7.85, N3.31, O15.11, found : 73.66, H8.11, N3.45, O14.71.