Synthesis of the enantiomer of the antidepressant tranylcypromine

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3505-3512

  Csuk, René ^a   Schabel, Magda J ^b   Von Scholz, Yvonne ^b  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

TRANYLCYPROMINE;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030561380     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00457-0     Document Type: Article

References (20)

1. 1 However, it is also conceivable that the enantiomer that is about to be discarded is modifying the activity of the other enantiomer.
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12. 11 Lowenthal, R. E.; Abiko, A.; Masamune, S., Tetrahedron Lett. 1990, 31, 6005-6008.
13. 12 Haefinger, W.; Klöppner, E., Helv. Chim. Acta 1982, 65, 1837-1852; Koskinen, A. M. P.; Munoz, L., J. Org. Chem. 1993, 58, 879-886;
14. 12 Haefinger, W.; Klöppner, E., Helv. Chim. Acta 1982, 65, 1837-1852; Koskinen, A. M. P.; Munoz, L., J. Org. Chem. 1993, 58, 879-886;
15. 13 The racemate has already been described: Baumgarten, H. E.; Smith, H. L.; Staklis, A., J. Org. Chem. 1975, 40, 3554-3561.
16. 14 Previously the formation of such carbamoyl azides during Curtius degradation has been observed: Ninomiya, K.; Shioiri, T.; Yamada, S., Chem. Pharm. Bull. 1974, 22, 1398-1404; Ninomiya, K.; Shioiri, T.; Yamada, S., Tetrahedron 1974, 30, 2151-2157;
17. 14 Previously the formation of such carbamoyl azides during Curtius degradation has been observed: Ninomiya, K.; Shioiri, T.; Yamada, S., Chem. Pharm. Bull. 1974, 22, 1398-1404; Ninomiya, K.; Shioiri, T.; Yamada, S., Tetrahedron 1974, 30, 2151-2157;
18. 15 Recently a sulfated cyclodextrine chiral stationary phase for HPLC has been described thus allowing the direct determination of 1 without the need of derivatization. Unfortunately, this material is not commercial available; Stalcup, A. M.; Gahm, K. H., Anal. Chem. 1996, 68, 1369-1374.
19. 16 Vince, R.; Turakhia, R. H.; Shannon, W. M.; Arnett, G., J. Med. Chem. 1987, 30, 2026-2030.
20. 17 Mori, A.; Arai, I.; Yamamoto, H.; Tetrahedron 1986, 42, 6447-6458.