A practical synthesis of enantiomerically pure N-benzyl-α-methyl benzylamine

Organic Process Research and Development

Volumn 4, Issue 6, 2000, Pages 594-595

  Huckabee, Brian K ^a   Lin, Sechoing ^a   Smith, Traci L ^a   Stuk, Timothy L ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034345929     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op000201n     Document Type: Article

References (12)

1. The amine 3 has been used successfully as a resolving agent, (a) Juaristi, E. Tetrahedron Asymmetry 1998, 9, 715.
2. (b) See also: Japanese Patent JP 05255180A, 1993.
3. Majewski, M.; Gleave, D. M. J. Org. Chem. 1992, 57(13), 3599-605.
4. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Walters, I. A. S.; Tetrahedron Asymmetery 1994, 5(1), 35-36.
5. Brintzinger, H.; Ringwaid, M.; Strumer, R. J. Am. Chem. Soc. 1999, 121, 1524.
6. Tani, K.; Onouchi. J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955.
7. Juaristi, E.; Murer, P.; Seebach, D. Synthesis 1993, 12, 1243-6.
8. Cain, C. M.; Cousins, R. P. C.; Coumbarides, G.; Simpkins, N. S. Tetrahedron 1990, 46, 523.
9. Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y. Chem. Pharm. Bull. 1979, 27, 7(11), 2795.
10. (b) Bourzat, J. D.; Comercon, A. Tetrahedron Lett., 1993 34, 6049.
11. The formation of the imine R-5 and the hydrogenation to give R-3 have been run at double this concentration at the 20 gm scale. Furthermore, water was not removed from the reaction prior to hydrogenation. The reaction behaved identically.
12. 2NH); 0.5 mL per minute, 254 nm. Elution time: 14.5 min. (R), 15.8 min. (S).