Alkyl substituent effects on pipecolyl amide isomer equilibrium: Efficient methodology for synthesizing enantiopure 6-alkylpipecolic acids and conformational analysis of their N-acetyl N'-methylamides

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1993-2002

  Swarbrick, Martin E ^a   Gosselin, Francis ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 TERT BUTYLPIPECOLINAMIDE; N ACETYL N METHYLPIPECOLINAMIDE; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; MOLECULAR INTERACTION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033583198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982181h     Document Type: Article

References (77)

1. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M. J. Am. Chem. Soc. 1987, 109, 5031.
2. Swindells, D. C. N.; White, P. S.; Findlay, J. A. Can. J. Chem. 1978, 56, 2491.
3. Anteunis, M. J. O.; Callens, R. E. A.; Tavernier, D. K. Eur. J. Biochem. 1975, 58, 259.
4. (a) Gupta, S.; Krasnof, S. B.; Roberts, D. W.; Renwick, J. A. A.; Brinen, L. S.; Clardy, J. J. Org. Chem. 1992, 57, 2306.
5. (b) Gupta, S.; Krasnof, S. B.; Roberts, D. W.; Renwick, J. A. A.; Brinen, L. S.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 707.
6. Darkin-Rattray, S. J.; Gurnett, A. M.; Myers, R. W.; Dulski, P. M.; Crumley, T. M.; Allocco, J. J.; Cannova, C.; Meinke, P. T.; Colletti, S. L.; Bednarek, M. A.; Singh, S. B.; Goetz, M. A.; Dombrowski, A. W.; Polishook, J. D.; Schmatz, D. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13143.
7. (a) Liard, F.; Ghiro, E.; Paris, W.; Yoakim, C. J. Pharm. Biomed. Anal. 1995, 14, 151.
8. (b) Copeland, T. D.; Wondrak, E. M.; Tozser, J.; Roberts, M. M.; Oroszlan, S. Biochem. Biophys. Res. Commun. 1990, 169, 310.
9. (a) Kern, D.; Schutkowski, M.; Drakenberg, T. J. Am. Chem. Soc. 1997, 119, 8403.
10. (b) Ando, S.; Ikuhara, T.; Kamata, T.; Sasaki, Y.; Hisanga, S.-i.; Kishimoto, T.; Ito, H.; Inagaki, M. J. Biochem. 1997, 122, 409.
11. Wu, W.-J.; Raleigh, D. P. J. Org. Chem. 1998, 63, 6689.
12. Couper, L.; McKendrick, J. E.; Robins, D. J.; Chrystal, E. J. T. Bioorg. Med. Chem. Lett. 1994, 4, 2267.
13. Mannaioni, G.; Alesiani, M.; Carlá, V.; Natalini, B.; Marinozzi, M.; Pelliciari, R.; Moroni, F. Eur. J. Pharmacol. 1994, 251, 201.
14. Ornstein, P. L.; Schoepp, D. D.; Arnold, M. B.; Jones, N. D.; Deeter, J. B.; Lodge, D.; Leander, J. D. J. Med. Chem. 1992, 35, 3111.
15. Reviewed in: O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637.
16. Ohtani, B.; Tsuru, S.; Nishimoto, S.-i.; Kagiya, T.; Izawa, K. J. Org. Chem. 1990, 55, 5551.
17. Beausoleil, E.; Lubell, W. D. J. Am. Chem. Soc. 1996, 118, 12902.
18. Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437.
19. Preliminary results have been reported in part in Gosselin, F.; Swarbrick, M. E.; Lubell, W. D. In Peptides 1998 (Proceedings of the 25th European Peptide Symposium); Bajusz, S., Hudecz, F., Eds; Akadémia Kiadó: Budapest, Hungary, 1999, in press.
20. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633.
21. Syntheses of 3-substituted pipecolates include the following: (a) Agami, C.; Bihan, D.; Hamon, L.; Puchot-Kadouri, C. Tetrahedron 1998, 54, 10309.
22. (b) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 566.
23. (c) Battistini L.; Zanardi F.; Rassu G.; Spanu P.; Pelosi G.; Fava G. G.; Ferrari M. B.; Casiraghi G. Tetrahedron: Asymmetry 1997, 8, 2975.
24. (d) Makara, G. M.; Marshall, G. R. Tetrahedron Lett. 1997, 38, 5069.
25. (e) Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001.
26. (f) Subramanyam, C.; Chatterjee, S.; Mallamo, J. P. Tetrahedron Lett. 1996, 37, 459.
27. (g) Greck, C.; Ferreira, F.; Genêt, J. P. Tetrahedron Lett. 1996, 37, 2031.
28. Syntheses of 4-substituted pipecolates include the following: (a) Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
29. (b) Bousquet, Y.; Anderson, P. C.; Bogri, T.; Duceppe, J.-S.; Grenier, L.; Guse, I. Tetrahedron 1997, 53, 15671.
30. (c) Golubev, A. S.; Sewald, N.; Burger, K. Tetrahedron 1996, 52, 14757.
31. (d) Machetti, F.; Cordero, F. M.; De Sarlo, F.; Guarna, A.; Brandi, A. Tetrahedron Lett. 1996, 37, 4205.
32. (e) Gillard, J.; Abraham, A.; Anderson, P. C.; Beaulieu, P. L.; Bogri, T.; Bousquet, Y.; Grenier, L.; Guse, I.; Lavallée, P. J. Org. Chem. 1996, 61, 2226.
33. (f) Skiles, J. W.; Giannousis, P. P.; Fales, K. R. Bioorg. Med. Chem. Lett. 1996, 6, 963.
34. Syntheses of 5-substituted pipecolates include the following: (a) Murray, P. J.; Starkey, I. D. Tetrahedron Lett. 1996, 37, 1875.
35. (b) Hoarau, S.; Fauchère, J. L.; Pappalardo, L.; Roumestant, M. L.; Viallefont, P. Tetrahedron: Asymmetry 1996, 7, 2585.
36. (c) Adams, D. R.; Bailey, P. D.; Collier, I. D.; Heffernan, J. D.; Stokes, S. Chem. Commun. 1996, 349.
37. (d) Ezquerra, J.; Pedregal, C.; Escribano, A.; Carreño, M. C.; Ruano, J. L. G. Tetrahedron Lett. 1995, 36, 3247.
38. Syntheses of optically active 6-substituted pipecolates include the following: enzymatic desymmetrisation (a) Chênevert, R.; Morin, M.-P. Tetrahedron: Asymmetry 1996, 9, 2161; diastereoselective additions to chiral iminium ions
39. (b) Ojima, I.; Tzamarioudaki, M.; Eguchi, M. J. Org. Chem. 1995, 60, 7078.
40. (c) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769.
41. (d) Ludwig, C.; Wistrand, L.-G. Acta Chem. Scand. 1994, 48, 367. For a racemic synthesis see ref 9.
42. Syntheses of multi-substituted pipecolates include the following: (a) Barluenga, J.; Aznar, F.; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918.
43. (b) Klumpe, M.; Dötz, K. H. Tetrahedron Lett. 1998, 39, 3683.
44. (c) Grandel, R.; Kazmaier, U.; Rominger, F. J. Org. Chem. 1998, 63, 4524.
45. (d) Ho, B.; Zabriskie, T. M. Bioorg. Med. Chem. Lett. 1998, 8, 739.
46. (e) Herdeis, C.; Heller, E. Tetrahedron: Asymmetry 1997, 8, 1115.
47. (f) Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009.
48. (g) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1997, 789.
49. (h) Hanessian, S.; Reinhold: U.; Gentile, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1881.
50. Cox, R. J. Nat. Prod. Rep. 1996, 13, 29.
51. (a) Humphrey, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467.
52. (b) Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55 ,3068.
53. (c) Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017.
54. (d) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164.
55. Paz, M. M.; Sardina, J. F. J. Org. Chem. 1993, 58, 6990.
56. 5,6-Dialkylpipecolates have also been prepared using this methodology: Swarbrick, M. E.; Lubell, W. D. manuscript in preparation.
57. Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463.
58. 2 = 0.0584 for all data; GOF = 0.990. The author has deposited the atomic coordinates for the structure of 5 with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
59. For a review, see d'Angelo, J. Tetrahedron 1976, 32, 2979.
60. Miller, M. J. J. Org. Chem. 1980, 45, 3131.
61. (a) Beausoleil, E.; L'Archevêque, B.; Bélec, L.; Atfani, M.; Lubell, W. D. J. Org. Chem. 1996, 61, 9447.
62. (b) Ibrahim, H. H.; Lubell, W. D. J. Org. Chem. 1993, 58, 6438.
63. Buu-Höi, Ng. Ph. Justus Liebigs Ann. Chem. 1944, 556, 1.
64. Although it is listed in the Aldrich Chemical Co. 1996-97 catalogue for $40.70 Canadian per gram, we synthesize >250 g batches of 9-bromo-9-phenylfluorene from inexpensive fluorenone, bromobenzene, butyllithium and HBr in >80% yield using the convenient protocol described in: Jamison, T. F.; Lubell, W. D.; Dener, J. M.; Krisché, M. J.; Rapoport, H. Org. Synth. 1992, 71, 220.
65. Monographs include the following: (a) Rylander, P. N. Catalytic Hydrogenation In Organic Synthesis; Academic Press: New York, 1979.
66. (b) Rylander, P. N. Catalytic Hydrogenation Over Platinum Metals; Academic Press: New York, 1967.
67. (a) Lubell, W.; Rapoport, H. J. Org. Chem. 1989, 54, 3824.
68. (b) Park, K. H.; Rapoport, H. J. Org. Chem. 1994, 59, 394.
69. Davis, F. A.; Szewczyk, J. M. Tetrahedron Lett. 1998, 39, 5951.
70. (a) Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
71. 6 salt, substantiates a guanidinium-1-N-oxide salt for TBTU: (b) Abdelmoty, I.; Albericio, F.; Carpino, L. A.; Foxman, B.; Kates, S. A. Lett. Peptide Sci. 1994, 1, 57.
72. Stein, R. L. Adv. Protein Chem. 1993, 44, 1.
73. Sandström, J. Dynamic NMR Spectroscopy, Academic Press: London, 1982, ch. 6, p 79.
74. Paulsen, H.; Todt, K. Chem. Ber. 1967, 100, 3385.
75. Keller, R. N.; Wycoff, H. D. Inorg. Synth. 1946, 2, 1.
76. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
77. Kliegl, A. Chem. Ber. 1905, 38, 284.