Synthesis of N-methyl secondary amines

Synthetic Communications

Volumn 33, Issue 8, 2003, Pages 1411-1416

  Kumpaty, Hephzibah J ^a   Williamson, John S ^b   Bhattacharyya, Sukanta ^c  

^a UNIVERSITY OF WISCONSIN WHITEWATER   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Argonaut Technologies   (United States)

Author keywords

Methylamine; Reductive alkylation; Sodium borohydride; Titanium(IV) isopropoxide

Indexed keywords

METHYLAMINE; SODIUM BOROHYDRIDE; TITANIUM;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0038642179     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018703     Document Type: Article

References (14)

1. 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; Main, B.G.; Tucker, H. Medicinal Chemistry, 2nd Ed.; Genellin, C.R., Roberts, S.M., Ed.; 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; Kirschbaum, J. Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press: New York, 1983; Vol. 12, p. 1.
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; Main, B.G.; Tucker, H. Medicinal Chemistry, 2nd Ed.; Genellin, C.R., Roberts, S.M., Ed.; 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; Kirschbaum, J. 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; Main, B.G.; Tucker, H. Medicinal Chemistry, 2nd Ed.; Genellin, C.R., Roberts, S.M., Ed.; 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; Kirschbaum, J. 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; Main, B.G.; Tucker, H. Medicinal Chemistry, 2nd Ed.; Genellin, C.R., Roberts, S.M., Ed.; 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; Kirschbaum, J. Analytical Profiles of Drug Substances; Florey, K., Ed.; Academic Press: New York, 1983; Vol. 12, p. 1.
5. Brown, A.R.; Rees, D.C.; Rankovic, Z.; Morphy, J.R. J. Am. Chem. Soc. 1997, 119, 3288; see Ref. 10 cited therein.
6. For example, see: Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; Bhattacharyya, S.; Neidigh, K.A.; Avery, M.A.; Williamson, J.S. Synlett 1999, 1781.
7. For example, see: Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; Bhattacharyya, S.; Neidigh, K.A.; Avery, M.A.; Williamson, J.S. Synlett 1999, 1781.
8. For example, see: Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; Bhattacharyya, S.; Neidigh, K.A.; Avery, M.A.; Williamson, J.S. Synlett 1999, 1781.
9. For some recent reviews on reductive aminations see: (a) Whitesell, J.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p.724; (b) Hutchins, R.O.; Hutchins, M.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, p. 25; (c) Gribble, G.W. Reductions in Organic Synthesis; Abdel-Majid, A.F., Ed.; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 167; (d) Abdel-Majid, A.F. Reductions in Organic Synthesis; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 201.
10. For some recent reviews on reductive aminations see: (a) Whitesell, J.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p.724; (b) Hutchins, R.O.; Hutchins, M.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, p. 25; (c) Gribble, G.W. Reductions in Organic Synthesis; Abdel-Majid, A.F., Ed.; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 167; (d) Abdel-Majid, A.F. Reductions in Organic Synthesis; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 201.
11. For some recent reviews on reductive aminations see: (a) Whitesell, J.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p.724; (b) Hutchins, R.O.; Hutchins, M.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, p. 25; (c) Gribble, G.W. Reductions in Organic Synthesis; Abdel-Majid, A.F., Ed.; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 167; (d) Abdel-Majid, A.F. Reductions in Organic Synthesis; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 201.
12. For some recent reviews on reductive aminations see: (a) Whitesell, J.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p.724; (b) Hutchins, R.O.; Hutchins, M.K. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, p. 25; (c) Gribble, G.W. Reductions in Organic Synthesis; Abdel-Majid, A.F., Ed.; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 167; (d) Abdel-Majid, A.F. Reductions in Organic Synthesis; ACS Symposium Series 641, American Chemical Society: Washington, DC, 1996; p. 201.
13. Neidigh, K.A.; Avery, M.A.; Williamson, J.S.; Bhattacharyya, S.J. Chem. Soc. Perkin Trans. 1 1998, 2527.
14. Seebach, D.; Hungerbuhler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Zueger, M. Synthesis 1982, 138.