A new Reagent for the Selective, High-Yield n-Dealkylation of Tertiary Amines: Improved Syntheses of Naltrexone and Nalbuphine

Journal of Organic Chemistry

Volumn 49, Issue 11, 1984, Pages 2081-2082

  Olofson, R A ^a   Martz, Jonathan T ^a   Senet, Jean Pierre ^b   Piteau, Marc ^b   Malfroot, Thierry ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b Soc Natl des Poudres et Explosifs   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NALBUPHINE; NALTREXONE;

CHLOROFORMIC ACID 1 CHLOROETHYL ESTER; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0021260262     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00185a072     Document Type: Article

References (17)

1. Olofson, R. A.; Schnur, R. C.; Bunes, L.; Pepe, J. P. Tetrahedron Lett. 1977, 1567.
2. Cagnon, G.; Piteau, M.; Senet, J.-P.; Olofson, R. A.; Martz, J. T. Eur. Pat. Appl. EP 40153 [Chem. Abstr. 1982, 96, 142281y].
3. Olofson, R. A.; Yamamoto, Y. S.; Wancowicz, D. J. Tetrahedron Lett. 1977, 1563.
4. Olofson, R. A.; Schnur, R. C. Tetrahedron Lett. 1977, 1571.
5. Hageman, H. A. Org. React. (N.Y.) 1953, 7, 198.
6. Bachelet, J.-P.; Caubere, P. J. Org. Chem. 1982, 47, 234.
7. Montzka, T. A.; Matiskella, J. D.; Partyka, R. A. Tetrahedron Lett. 1974, 1325.
8. Freund, M.; Speyer, E. J. Prakt. Chem. 1916, 94, 135.
9. Takamine Kenkusho Nempo 1960, 12, 56.
10. Lutz, R. E.; Small, L. J. Org. Chem. 1939, 4, 220.
11. Olofson, R. A.; Pepe, J. P. Tetrahedron Lett. 1977, 1575, 2918.
12. Johnson, M. R.; Milne, G. M. In “Burger's Medicinal Chemistry”, Part III, 4th ed.; Wolff, M. E., Ed.; Wiley: New York, 1981; pp 699-758.
13. Olofson, R. A.; Pepe, J. P. U.S. Patent 4141897 (Chem. Abstr. 1979, 91, 57263w);
14. Olofson, R. A.; Pepe, J. P. U.S. Patent 4161597 (Chem. Abstr. 1980, 92, 22671w).
15. Pachter, I. J.; Soloway, H. Canadian Patent 913077.
16. Pachter, I. J.; Soloway, H. Chem. Abstr. 1972, 77, 105601.
17. Rice, K. C. J. Med. Chem. 1977, 20, 164.