Selective monoalkylation of ammonia: A high throughput synthesis of primary amines

Synlett

Volumn , Issue 11, 1999, Pages 1781-1783

  Bhattacharyya, Sukanta ^a,c   Neidigh, Kurt A ^b   Avery, Mitchell A ^b   Williamson, John S ^b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Argonaut Technologies   (United States)

Author keywords

Primary amines; Reductive amination; Titanium (IV) isopropoxide

Indexed keywords

AMINE; AMMONIA; SODIUM BOROHYDRIDE; TITANIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0032724354     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2946     Document Type: Article

References (31)

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2. For some leading references, see: Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds: Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643. A quarter of registered drugs contain amino functionality: Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288. Main, B.G.; Tucker, H. In Medicinal Chemistry, 2nd ed.; Genellin, C. R.; Roberts, S.M., Eds.; Academic Press: New York, 1993, p 187. Kukhar, V. P.; Svistunova, N. Yu.; Soloshonok, V. A.; Solodenko, V. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 284. Manchand, P. S.; Cerruti, R. L.; Martin, J. A.; Hill, C. H.; Merrett, J. H.; Keech, E.; Belshe, R. B.; Connell, E. V.; Sim, I. S. J. Med. Chem. 1990, 33, 1992. Kirschbaum, J. In Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press, New York, 1983, Vol. 12, p 1.
3. For some leading references, see: Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds: Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643. A quarter of registered drugs contain amino functionality: Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288. Main, B.G.; Tucker, H. In Medicinal Chemistry, 2nd ed.; Genellin, C. R.; Roberts, S.M., Eds.; Academic Press: New York, 1993, p 187. Kukhar, V. P.; Svistunova, N. Yu.; Soloshonok, V. A.; Solodenko, V. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 284. Manchand, P. S.; Cerruti, R. L.; Martin, J. A.; Hill, C. H.; Merrett, J. H.; Keech, E.; Belshe, R. B.; Connell, E. V.; Sim, I. S. J. Med. Chem. 1990, 33, 1992. Kirschbaum, J. In Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press, New York, 1983, Vol. 12, p 1.
4. For some leading references, see: Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds: Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643. A quarter of registered drugs contain amino functionality: Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288. Main, B.G.; Tucker, H. In Medicinal Chemistry, 2nd ed.; Genellin, C. R.; Roberts, S.M., Eds.; Academic Press: New York, 1993, p 187. Kukhar, V. P.; Svistunova, N. Yu.; Soloshonok, V. A.; Solodenko, V. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 284. Manchand, P. S.; Cerruti, R. L.; Martin, J. A.; Hill, C. H.; Merrett, J. H.; Keech, E.; Belshe, R. B.; Connell, E. V.; Sim, I. S. J. Med. Chem. 1990, 33, 1992. Kirschbaum, J. In Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press, New York, 1983, Vol. 12, p 1.
5. For some leading references, see: Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds: Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643. A quarter of registered drugs contain amino functionality: Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288. Main, B.G.; Tucker, H. In Medicinal Chemistry, 2nd ed.; Genellin, C. R.; Roberts, S.M., Eds.; Academic Press: New York, 1993, p 187. Kukhar, V. P.; Svistunova, N. Yu.; Soloshonok, V. A.; Solodenko, V. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 284. Manchand, P. S.; Cerruti, R. L.; Martin, J. A.; Hill, C. H.; Merrett, J. H.; Keech, E.; Belshe, R. B.; Connell, E. V.; Sim, I. S. J. Med. Chem. 1990, 33, 1992. Kirschbaum, J. In Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press, New York, 1983, Vol. 12, p 1.
6. For some leading references, see: Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds: Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643. A quarter of registered drugs contain amino functionality: Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288. Main, B.G.; Tucker, H. In Medicinal Chemistry, 2nd ed.; Genellin, C. R.; Roberts, S.M., Eds.; Academic Press: New York, 1993, p 187. Kukhar, V. P.; Svistunova, N. Yu.; Soloshonok, V. A.; Solodenko, V. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 284. Manchand, P. S.; Cerruti, R. L.; Martin, J. A.; Hill, C. H.; Merrett, J. H.; Keech, E.; Belshe, R. B.; Connell, E. V.; Sim, I. S. J. Med. Chem. 1990, 33, 1992. Kirschbaum, J. In Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press, New York, 1983, Vol. 12, p 1.
7. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
8. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
9. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
10. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
11. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
12. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
13. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
14. For reductive amination reviews, see: Emerson, W.S. Org. React. (N.Y.) 1948, 4, 174. Moore, M.L. Org. React. (N.Y.) 1949, 5, 301. Lane, C.F. Synthesis, 1975, 135. Hutchins, R.O.; Natale, N. Org. Prep. Proced. Int., 1979, 11, 201. Gribble, G.W.; Nutaitis, C.F. Org. Prep. Proced. Int., 1985, 17, 317. Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 6, p 724. Hutchins, R.O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 8, p 25. Abdel-Magid, A. F.; Maryanoff, C.A. In Reductions in Organic Synthesis, ACS Symposium Series 641, Abdel-Magid, A. F., Ed. American Chemical Society, Washington, D.C., 1996, p 202.
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16. th ed.; John Wiley & Sons, NY, 1992, p. 989.
17. th ed.; John Wiley & Sons, NY, 1992, p. 989.
18. th ed.; John Wiley & Sons, NY, 1992, p. 989.
19. th ed.; John Wiley & Sons, NY, 1992, p. 989.
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30. The corresponding reaction with aldehydes, however, did not provide primary amines; symmetrical secondary amines were obtained as the only products.
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