The conversion of amides to esters with Meerwein's reagent. Application to the synthesis of a carfentanil precursor

Synthetic Communications

Volumn 27, Issue 5, 1997, Pages 923-937

  Kiessling, Anthony J ^a,b   McClure, Cynthia K ^a,c  

^a UNIVERSITY OF DELAWARE   (United States)

^b SALISBURY UNIVERSITY   (United States)

^c MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARFENTANIL; PIPERIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031000575     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004212     Document Type: Article

References (35)

1. See Kintz, P.; Mangin, P.; Lugnier, A. A.; Chaumont, A. J. J. Chromatog., 1989, 489, 459; and references cited therein.
2. Janssen, P. A. J.; Van Daele, G. H. P.; U.S. Patent #4,179,569, Cl. 546-223;CO7D211/58; Granted 12/18/19 Appl. 558, 511, 3/14/75. CA92:P128743m.
3. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
4. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
5. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
6. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
7. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
8. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
9. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
10. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
11. For recent synthetic approaches see the following. (a) Taber, D.F.; Rahimizadeh, M. J. Org. Chem. 1992, 57, 4037. (b) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. Colapret, J. A.; Diamantidis, G.; Spencer, H. K.; Spaulding, T. C.; Rudo, F. G. J. Med. Chem. 1989, 32, 1968. Bagley, J. R.; Wynn, R. L.; Rudo, F. G.; Doorley, B. M.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 663. (e) Casey, A. F.; Huckstep, M. R.; J. Pharm. Pharmacol. 1988, 40, 605. (f) Janssens, F.; Torremans, J. Janssen, P. A. J. J. Med. Chem. 1986, 29, 2290. (g) Van Daele, P. G. H.; De Bruyn, M. F. L.; Sanczuk, S.; Agten, J. T. M.; Janssen, P. A. J. Arzneim-Forsch., 1976, 26, 1521-1531. (h) Van Beaver, W. F. M.; Niemegeers, C. J. F.; Janssen, P. A. J. Med. Chem. 1974, 17, 1047. Kudzma, L. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. J. Med. Chem. 1989, 32, 2534.
12. (a) Kishi, Y.; Fukuyama, T.; Aratani, M.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Suglura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9219.
13. (b) Crittenden, R. A.; Cooper, G. H. J. Chem. Soc. 1970, 49.
14. Hanessian, S. Tetrahedron Lett. 1967, 1549.
15. Muxfeldt, H.; Behling, J.; Grethe, G.; Rogalski, W. J. Am. Chem. Soc. 1967, 89, 4991.
16. (a) Smith, M. B.; Menezes, R. Syn. Comm. 1988, 18, 1625.
17. (b) Sheehan, J. C.; Nafissi-V, M. M. J. Org. Chem. 1970, 35, 4246.
18. (a) Schroeder, J. P.; Schroeder, D. C.; Hardin, J.; Marshall, J. K. J. Org. Chem. 1969, 34, 3332.
19. (b) Barthel, W. F.; Leon, J.; Hall, S. A. J. Org. Chem. 1954, 19, 485.
20. Pearl, I. A.; Beyer, D. L. J. Am. Chem. Soc. 1952, 74, 3188 and refs cited therein.
21. Rising, M. M.; Zee, T-W. J. Am. Chem. Soc. 1928, 50, 1208 and refs cited therein.
22. (a) Curphey, T. J. In Organic Syntheses, Collective Volumes; Noland, W. Ed.; John Wiley & Sons: New York, 1988, Vol. 6, 1019.
23. (b) Meerwein, H. In Organic Syntheses, Collective Volumes; Baumgarten, H. Ed.; John Wiley & Sons: New York, 1973, Vol. 5, p 1080.
24. Presumedly, loss of HCN during the course of the reaction was responsible for the low yield of product.
25. The following amides were synthesised according to known proceedures 9b Smith, P. A. S.; Ashby, B. J. Am. Chem. Soc. 1950, 72, 2503.
26. 9c Chodnekar, H. S.; Blum, J. E. J. Med. Chem. 1968, 11, 1023.
27. 9d McCabe, E. T.; Barthel, W. F.; Gerter, S. T.; Hall, S. A. J. Org. Chem. 1954, 19, 493.
28. 9e Ralston, A. W.; Pool, W. O. J. Org. Chem. 1943, 8, 473.
29. 9f D'Alelio, G. F., Reid, E. E. J. Am. Chem. Soc. 1937, 59, 109.
30. Compounds 9a and 9h are available from Aldrich.
31. CRC Handbook of Chemistry and Physics, 64th ed.; Weast, R. C., Ed.; CRC Inc.: Boca Raton, FL, 1983.
32. Aldrich 24586-0.
33. Aldrich 23459-1.
34. Lancaster 1407.
35. Lancaster 5314.