Efficient and mild procedure for reductive methylation of amines using N-methylpiperidine zinc borohydride

Synthetic Communications

Volumn 36, Issue 23, 2006, Pages 3609-3615

  Alinezhad, Heshmatollah ^a   Tajbakhsh, Mahmood ^a   Zamani, Reza ^a  

^a UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Amines; Formaldehyde; Reductive methylation; ZBNMPP

Indexed keywords

AMINE; BORANE DERIVATIVE; METHANOL; N METHYLPIPERIDINE ZINC BOROHYDRIDE; TERTIARY AMINE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; METHYLATION; ROOM TEMPERATURE;

EID: 33845617986     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600943667     Document Type: Article

References (25)

1. (a) Baxter, E. W.; Reitz, A. B. Org. React. 2002, 59, 1;
2. (b) Manchand, P. S.; Cerruti, R. L.; Martin, J. A. J. Med. Chem. 1990, 33, 1992;
3. (c) Askin, D.; Wallace, M. A.; Reamer, R. A.; Volant, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771.
4. (a) Jung, Y. J.; Bae, J. W.; Park, E. S.; Chang, Y. M.; Yoon, C. M. Tetrahedron 2003, 59, 10331;
5. (c) Pelter, A.; Rosser, R. M. J. Chem. Soc., Perkin Trans. 1 1985, 50, 1927;
6. (d) Selva, M.; Tundo, P. Tetrahedron Lett. 2003, 44, 8139.
7. (a) Sondengam, B. L.; Hemo, J. H.; Charles, G. Tetrahedron Lett. 1973, 14, 261;
8. (b) Boldrini, P.; Panunizo, M.; Ronchi, A. Synthesis 1974, 261.
9. (a) Gribble, G. W.; Lord, P. D.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812;
10. (b) Verado, G.; Jasinski, J. M.; Pellicone, J. T.; Panetta, J. A. Synthesis 1978, 766.
11. Kishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315.
12. Kim, S.; Oh, C. H.; Ko, J. S.; Ahn, K. H.; Kim, Y. J. J. Org. Chem. 1985, 50, 1927.
13. (a) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928;
14. (b) Miriyala, B.; Bhattacharyya, S.; Williamson, J. S. Tetrahedron 2004, 60, 1463;
15. (c) Base, J. W.; Lee, S. H.; Cho, Y. J.; Yoon, C. M. J. Chem. Soc., Perkin Trans. 1 2000, 145.
16. Firouzabadi, H.; Iranpoor, N.; Alinezhad, H. Bull. Chem. Soc. Jpn. 2003, 76, 143.
17. (a) Pine, S. H.; Sanchez, B. L. J. Org. Chem. 1971, 36, 829;
18. (b) Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
19. Alinezhad, H.; Tajbakhsh, M.; Zamani, R. Synlett 2006, 431.
20. Giumanini, A. G.; Chiavari, G.; Musiani, M. M.; Rossi, P. Synthesis 1980, 743.
21. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673.
22. Katritzky, A. R.; Rachwal, S.; Wu, J. Can. J. Chem. 1990, 68, 465.
23. Barton, D. H.; Ozbalik, N.; Ramesh, M. Tetrahedron Lett. 1988, 29, 857.
24. Gribble, G. W.; Nutaitis, C. F. Synthesis 1987, 709.
25. Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401.