Direct reductive amination of aldehyde bisulfite adducts induced by 2-picoline borane: Application to the synthesis of a DPP-IV inhibitor

Journal of Organic Chemistry

Volumn 78, Issue 4, 2013, Pages 1655-1659

  Faul, Margaret ^a   Larsen, Rob ^a,b   Levinson, Adam ^a,c   Tedrow, Jason ^a   Vounatsos, Filisaty ^a  

^a AMGEN INC   (United States)

^b ALCON RESEARCH LTD   (United States)

^c Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PICOLINE; PROTIC SOLVENTS; REACTION MEDIA; REDUCTIVE AMINATION;

AMINES;

ALDEHYDES;

1 (2 (CYCLOHEXYLAMINO)ACETYL) PYRROLIDINE 2 CARBONITRILE; 1 (2 (PHENYLAMINO)ACETYL)PYRROLIDINE 2 CARBONITRILE; 1 PHENYL 2 (PHENYLAMINO)ETHANONE; 2 (HEXYLAMINO) 1 MORPHOLINOETHANONE; 2 PICOLINE BORANE; ALDEHYDE; ALDEHYDE BISULFITE; BISULFITE; DIPEPTIDYL PEPTIDASE IV INHIBITOR; ETHYLANILINE; N BENZYL 2 METHYLPROPAN 2 AMINE; N BENZYLANILINE; N BENZYLHEXAN 1 AMINE; REDUCING AGENT; SOLVENT; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE; THERMOSTABILITY;

ALDEHYDES; ALKYLATION; AMINATION; AMINES; BORANES; DIPEPTIDYL PEPTIDASE 4; MORPHOLINES; PICOLINES; SULFITES;

EID: 84873973288     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3023878     Document Type: Article

References (27)

1. March, J. Advanced Organic Chemistry, 2 nd ed.; McGraw-Hill: New York, 1977; p 816.
2. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 1206-1214
3. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 1228-1235
4. Kjell, D. P.; Slattery, B. J.; Semo, M. J. J. Org. Chem. 1999, 64, 5722-5724
5. Ragan, J. A.; am Ende, D, J.; Brenek, S. J.; Eisenbeis, S. A.; Singer, R. A.; Tickner, D. L.; Teixeira, J. T., Jr.; Vanderplas, B. C.; Weston, N. Org. Process Res. Dev. 2003, 7, 155-160
6. Pandit, C. R.; Mani, N. S. Synthesis 2009, 23, 4032-4036
7. For an example of a bisulfite adduct used directly in a catalytic enantioselective hetero-Diels-Alder reaction, see: He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817-3820
8. For an example of a bisulfite adduct used directly in a diastereoselective Strecker reaction, see: Seki, M.; Hatsudab, M.; Yoshida, S. Tetrahedron Lett. 2004, 45, 6579-6581
9. For the synthesis and reported instability of the morpholino phenyl glyoxal substrate, see: Liu, Q.; Perreault, S.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14066-14067
10. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862
11. Baxter, E. W.; Reitz, A. B. Organic Reactions; John Wiley & Sons, Inc., New York, 2002; Vol. 59, p 1.
12. Matos, K.; Burkhardt, E. R. Pharmaceutical Process Chemistry; Shioiri, T.; Izawa, K.; Konoike, T., Eds.; Wiley-VCHVerlag: Weinheim, 2011; p 127.
13. Pelter, A.; Rosser, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 717
14. Moormann, A. E. Synth. Commun. 1993, 23, 789
15. Brown, H. C.; Kanth, J. V. B.; Dalvi, P. V.; Zaidlewicz, M. J. Org. Chem. 1999, 64, 6263-6274
16. Bomann, M. D.; Guch, I. C.; DiMare, M. J. Org. Chem. 1995, 60, 5995-5996
17. Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. Tetrahedron 2004, 60, 7899
18. Kikugawa, Y. Patent JP 2004256511, 2004.
19. Burkhardt, E. R.; Coleridge, B. M. Tetrahedron Lett. 49 2008, 49, 5152-5155
20. Pyridine borane decomposes at temperatures >54 C, which precluded further optimization of this reagent. Amine Borane; Callery Chemical Technical Bulletin, 2002, p 9.
21. Pandit, C. R.; Mani, N. S. Synthesis 2009, 23, 4032-4036
22. Hollmann, D.; Bahn, S.; Tillack, A.; Beller, M. Angew. Chem., Int. Ed. 2007, 46, 8291-8294
23. Shao-Hua, X.; Jian, X.; Hong-Qiu, Y.; Pei-Qiang, H. Synlett 2010, 12, 1829-1832
24. Lakner, F. J.; Parker, M. A.; Rogovoy, B.; Khvat, A.; Ivachtchenko, A. Synthesis 2009, 12, 1987-1990
25. Largeron, M.; Fleury, M.-B. Org. Lett. 2009, 11, 883-886
26. Villhauer, E. B.; Brinkman, J. A.; Naderi, G. B.; Burkey, B. F.; Dunning, B. E.; Prasad, K.; Mangold, B. L.; Russell, M. E.; Hughes, T E. J. Med. Chem. 2003, 46, 2774-2789
27. Yang, X.; Zhao, L.; Fox, T.; Wang, Z.-W.; Berke, H. Angew. Chem., Int. Ed. 2010, 49, 2058-2062