A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine

Organic Letters

Volumn 15, Issue 21, 2013, Pages 5594-5597

  Mellem, Kevin T ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHETAMINE; AMPHETAMINE DERIVATIVE; BENZYL DERIVATIVE; PSEUDOEPHENAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMPHETAMINE; AMPHETAMINES; BENZYL COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84887056372     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402815d     Document Type: Article

References (22)

1. Morales, M. R.; Mellem, K. T.; Myers, A. G. Angew. Chem., Int. Ed. 2012, 51, 4568-4571
2. Medley, J. W.; Movassaghi, M. Angew. Chem., Int. Ed. 2012, 51, 4572-4576
3. Hugelshofer, C. L.; Mellem, K. T.; Myers, A. G. Org. Lett. 2013, 15, 3134-3137
4. Yamashita, J.; Kawahara, H.; Ohashi, S.; Honda, Y.; Kenmotsu, T.; Hashimoto, H. Tech. Rep. Tohuku University 1983, 48, 211-219
5. Meyers, A. I.; Marra, J. M. Tetrahedron Lett. 1985, 26, 5863-5866
6. Lour, R.; Mi, A.; Jiang, Y.; Qin, Y.; Li, Z.; Fu, G.; Chan, A. S. C. Tetrahedron 2000, 56, 5857-5863
7. Wheatley, W. B.; Fitzgibbon, W. E.; Cheney, L. C. J. Org. Chem. 1953, 18, 1564-1571
8. Hahn, W. E.; Bartnik, R.; Mloston, G. Acta Pol. Pharm. 1979, 36, 619-620
9. Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1996, 61, 3888-3889
10. Murata, K.; Okano, K.; Miyagi, M.; Iwane, H.; Noyori, R.; Ikariya, T. Org. Lett. 1999, 1, 1119-1121
11. Touge, T.; Hakamata, T.; Nara, H.; Kobayashi, T.; Sayo, N.; Saito, T.; Kayaki, Y.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 14960-14963
12. Reductive amination of benzil in the presence of methylamine and a platinum catalyst has been reported to form ephenamine: Skita, A.; Keil, F. Manufacture of Aminoalcohols. U.K. Patent 313,217, July 24, 1930.
13. Alcaide, B.; López-Mardomingo, C.; Pérez-Ossorio, R.; Plumet, J. J. Chem. Soc., Perkin Trans. 2 1983, 1649-1653
14. Haro-Ramos, R.; Jimenez-Tebar, A.; Pérez-Ossario, R.; Plumet, J. Tetrahedron Lett. 1979, 20, 1355-1356
15. Alcaide, B.; Fernández de la Pradilla, R.; López- Mardomingo, C.; Pérez-Ossorio, R.; Plumet, J. J. Org. Chem. 1981, 46, 3234-3238
16. Alcaide, B.; Dominguez, G.; López-Mardomingo, C.; Pérez-Ossorio, R.; Plumet, J. J. Chem. Soc., Perkin Trans. 2 1986, 99-103
17. For a comprehensive guide to the optical resolution of racemic compounds via formation of diastereomeric salts, see: CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation; Kozma, D., Ed.; CRC Press: Boca Raton, FL, 2002.
18. Erlenmeyer, E.; Arnold, A. Justus Liebigs Ann. Chem. 1904, 337, 307-328
19. Manske, R. H. F.; Johnson, T. B. J. Am. Chem. Soc. 1929, 51, 1906-1909
20. Weijlard, J.; Pfister, K., III; Swanezy, E. F.; Robinson, C. A.; Tishler, M. J. Am. Chem. Soc. 1951, 73, 1216-1218
21. Saigo, K.; Sugiura, I.; Shida, I.; Tachibana, K.; Hasegawa, M. Bull. Chem. Soc. Jpn. 1986, 59, 2915-2916
22. A similar process has been reported to transform ephedrine to pseudoephedrine: Chou, T. Q. J. Biol. Chem. 1926, 70, 109-114