Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3849-3862

  Abdel Magid, Ahmed F ^a   Carson, Kenneth G ^a   Harris, Bruce D ^a   Maryanoff, Cynthia A ^a   Shah, Rekha D ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000844109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960057x     Document Type: Article

References (57)

1. Presented in part at the 33rd ACS National Organic Symposium, Bozeman, Mo, June 1993, Paper A-4. Preliminary communications: (a) Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595. (b) Abdel-Magid, A. F.; Maryanoff, C. A. Synlett 1990, 537.
2. Presented in part at the 33rd ACS National Organic Symposium, Bozeman, Mo, June 1993, Paper A-4. Preliminary communications: (a) Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595. (b) Abdel-Magid, A. F.; Maryanoff, C. A. Synlett 1990, 537.
3. The formation of imines or iminium ions was reported as possible intermediates in reductive amination reactions in catalytic hydrogenation methods, see (a) Emerson, W. S. Org. React. 1948, 4, 174 and references therein. It was also proposed in hydride methods, see (b) Schellenberg, K. A. J. Org. Chem. 1963, 28, 3259.
4. The formation of imines or iminium ions was reported as possible intermediates in reductive amination reactions in catalytic hydrogenation methods, see (a) Emerson, W. S. Org. React. 1948, 4, 174 and references therein. It was also proposed in hydride methods, see (b) Schellenberg, K. A. J. Org. Chem. 1963, 28, 3259.
5. Tadanier, J.; Hallas, R.; Martin, J. R.; Stanaszek, R. S. Tetrahedron 1981, 37, 1309
6. (a) Emerson, W. S.; Uraneck, C. A. J. Am. Chem. Soc. 1941, 63, 749.
7. (b) Johnson, H. E.; Crosby, D. G. J. Org. Chem. 1962, 27, 2205.
8. (c) Klyuev, M. V.; Khidekel, M. L. Russ. Chem. Rev. 1980, 49, 14.
9. Skita, A.; Keil, F. Chem. Ber. 1928, 61B, 1452.
10. Roe, A.; Montgomery, J. A. J. Am. Chem. Soc. 1953, 75, 910.
11. Rylander, P. N. In Catalytic Hydrogenation over Platinum Metals; Academic Press, New York, 1967; p 128.
12. Rylander, P. N. In Catalytic Hydrogenation over Platinum Metals; Academic Press, New York, 1967; p 21.
13. For a recent review on reduction of C=N compounds with hydride reagents see: Hutchins, R. O., Hutchins, M. K. Reduction of C=N to CHNH by Metal Hydrides. In Comprehensive Organic Synthesis; Trost, B. N., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 8.
14. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
15. Borch, R. F., Durst, H. D. J. Am. Chem. Soc. 1969, 91, 3996.
16. (a) Hutchins, R. O.; Natale, N. R. Org. Prep. Proced. Int. 1979, 11(5), 201.
17. (b) Lane, C. F. Synthesis 1975, 135.
18. Occasional use of weakly basic or nonbasic amines was reported, see for example: (a) Pelter, A., Rosser, R. M., Mills, S. J. Chem. Soc., Perkin Trans. 1 1984, 717. (b) Mattson, R. J., Pham, K. M.; Leuek, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552. (c) Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673. (d) Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Moracci, F. M. J. Org. Chem. 1975, 40, 3453.
19. Occasional use of weakly basic or nonbasic amines was reported, see for example: (a) Pelter, A., Rosser, R. M., Mills, S. J. Chem. Soc., Perkin Trans. 1 1984, 717. (b) Mattson, R. J., Pham, K. M.; Leuek, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552. (c) Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673. (d) Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Moracci, F. M. J. Org. Chem. 1975, 40, 3453.
20. Occasional use of weakly basic or nonbasic amines was reported, see for example: (a) Pelter, A., Rosser, R. M., Mills, S. J. Chem. Soc., Perkin Trans. 1 1984, 717. (b) Mattson, R. J., Pham, K. M.; Leuek, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552. (c) Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673. (d) Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Moracci, F. M. J. Org. Chem. 1975, 40, 3453.
21. Occasional use of weakly basic or nonbasic amines was reported, see for example: (a) Pelter, A., Rosser, R. M., Mills, S. J. Chem. Soc., Perkin Trans. 1 1984, 717. (b) Mattson, R. J., Pham, K. M.; Leuek, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552. (c) Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673. (d) Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Moracci, F. M. J. Org. Chem. 1975, 40, 3453.
22. (a) The product from large scale reduction of the imine (i) with sodium cyanoborohydride was contaminated with cyanide.
23. (b) A similar result was reported recently: Moormann, A. E. Synth. Commun. 1993, 23, 789. (Matrix Presented)
24. For information on the safety data and health hazards associated with sodium cyanoborohydride see: The Sigma-Aldrich Library of Chemical Safety Data, 1st ed.; Lenga, R. E., Ed., Sigma-Aldrich Corp.: Milwaukee, 1985, p 1609.
25. (a) Yoon, N. M.; Kim, E. G.; Son, H. S.; Choi, J. Synth. Commun. 1993, 23, 1595.
26. (b) Micovic, I. V.; Ivanovic, M. D.; Piatak, D. M.; Bojic, V. Dj. Synthesis 1991, 1043.
27. (c) Brussee, J.; van Benthem, R. A. T. M.; Kruse, C. G.; van der Gen, A. Tetrahedron: Asymmetry 1990, 1, 163.
28. (d) Bhattacharyya, S.; Chatterjee, A.; Duttachowdhhury, S. K. J. Chem. Soc., Perkin Trans. 1 1994, 1.
29. (a) Pienemann, T.; Schafer, H.-J. Synthesis 1987, 1005.
30. (b) Smirnov, Yu. D.; Tomilov, A. P. J. Org. Chem. U.S.S.R. 1992, 28(1), 42.
31. (c) Smirnov, Yu. D.; Pavlichenko, V. F.; Tomilov, A. P. J. Org. Chem. U.S.S.R. 1992, 28(3), 374.
32. (a) Gribble, G. W.; Ferguson, D. C. J. Chem. Soc., Chem. Commun. 1975, 535.
33. (b) Nutaitis, C. F.; Gribble, G. W. Tetrahedron Lett. 1983, 24, 4287.
34. (c) Gribble, G. W. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed., John Wiley and Sons: New York, 1995; Vol. 7, p 4649.
35. See for example: (a) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273. (b) Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939. (c) Evans, D. A., Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
36. See for example: (a) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273. (b) Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939. (c) Evans, D. A., Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
37. See for example: (a) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273. (b) Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939. (c) Evans, D. A., Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
38. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proced. Int. 1985, 17, 317.
39. Earlier work by Gribble et al. demonstrated the potential of triacyloxyborohydrides generated from NaBR, in neat liquid carboxylic acids in reductive alkylation of amines: (a) Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812. (b) Gribble, G. W.; Jasinski, J. M.; Pellicone, J. T.; Panetta, J. A. Synthesis 1978, 766.
40. Earlier work by Gribble et al. demonstrated the potential of triacyloxyborohydrides generated from NaBR, in neat liquid carboxylic acids in reductive alkylation of amines: (a) Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812. (b) Gribble, G. W.; Jasinski, J. M.; Pellicone, J. T.; Panetta, J. A. Synthesis 1978, 766.
41. 21a
42. 3-CN slightly favor the axial approach, see: (a) Wrobel, J. E.; Ganem, B. Tetrahedron Lett. 1981, 22, 3447. (b) Hutchins, R. o.; Markowitz, M. J. Org. Chem. 1981, 46, 3571. (c) Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. (d) Hutchins, R. O.; Adams, J.; Rutledge, M. C. J. Org. Chem. 1995, 60, 7396.
43. 3-CN slightly favor the axial approach, see: (a) Wrobel, J. E.; Ganem, B. Tetrahedron Lett. 1981, 22, 3447. (b) Hutchins, R. o.; Markowitz, M. J. Org. Chem. 1981, 46, 3571. (c) Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. (d) Hutchins, R. O.; Adams, J.; Rutledge, M. C. J. Org. Chem. 1995, 60, 7396.
44. 3-CN slightly favor the axial approach, see: (a) Wrobel, J. E.; Ganem, B. Tetrahedron Lett. 1981, 22, 3447. (b) Hutchins, R. o.; Markowitz, M. J. Org. Chem. 1981, 46, 3571. (c) Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. (d) Hutchins, R. O.; Adams, J.; Rutledge, M. C. J. Org. Chem. 1995, 60, 7396.
45. 3-CN slightly favor the axial approach, see: (a) Wrobel, J. E.; Ganem, B. Tetrahedron Lett. 1981, 22, 3447. (b) Hutchins, R. o.; Markowitz, M. J. Org. Chem. 1981, 46, 3571. (c) Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. (d) Hutchins, R. O.; Adams, J.; Rutledge, M. C. J. Org. Chem. 1995, 60, 7396.
46. Chemical shift assignments of individual protons were arrived at by COSY, HETCOR, and Inverse HMBC NMR experiments. The stereochemistry of N-phenyl-3-aminotropane and N-benzyl-3-aminotropane was assigned based on 1D NOE and coupling experiments. The assignments were in line with other literature reports; cf. Bagley, J. R.; Riley, T. N. J. Hetrocycl. Chem. 1977, 14, 599 and references therein.
47. For a discussion of the dialkylation side reactions involving γ-and δ-amino esters with aldehydes and a mechanistic explanation, see: Abdel-Magid, A. F.; Harris, B. D.; Maryanoff, C. A. Synlett 1994, 81.
48. The progress of these reactions was followed by GC. Linear standard curves of the response factors by GC areas of starting materials and expected products were determined to allow the quantitative measurements of their concentrations in the reaction mixtures.
49. (a) Albert, A.; Serjeant, E. P. In The Determination of Ionization Constants; Chapman and Hall: London, 1971; p 91.
50. (b) Yates, K; Wai, H. J. Am. Chem. Soc. 1964, 86, 5408.
51. Duriatti, A.; Bouvier-Nave, P.; Benveniste, P.; Schuber, F.; Delprino, L.; Balliano, G.; Cattel, L. Biochem. Pharmacol. 1985, 34, 2765.
52. Ceruti, M.; Balliano, G.; Viola, F.; Cattel; L.; Gerst, N.; Schuber, F. Eur. J. Med. Chem. 1987, 22, 199.
53. Campbell, J. B.; Lavagnino, E. P. In Catalysis in Organic Syntheses; Jones, W. H., Ed.; Academic Press: New York, 1980; p 43.
54. 4 in diglyme at 60°C or in ethanol at 25°C)] was reported recently:
55. (b) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401.
56. (c) Bhattacharyya, S. Synlett 1994, 1029;
57. (d) Bhattacharyya, S. Synth. Commun. 1996, 25, 9.