Efficient synthesis of (R)-6-benzyloxycarbonylamino-1-methyl-4-(3- methyl-benzyl)hexahydro-1,4-diazepine. 2. Novel formation of hexahydro-1,4- diazepine ring using 1,2,3-trisubstituted aminopropane derivative and glyoxal

Tetrahedron

Volumn 54, Issue 36, 1998, Pages 10671-10676

  Harada, Hiroshi ^a   Morie, Toshiya ^a   Suzuki, Toshifumi ^a   Yoshida, Toyokichi ^a   Kato, Shiro ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 BENZYLOXYCARBONYLAMINO 1 METHYL 4 (3 METHYLBENZYL)HEXAHYDRO 1,4 DIAZEPINE; AMIDE; DIAZEPINE DERIVATIVE; GLYOXAL; N [1 METHYL 4 (3 METHYLBENZYL)HEXAHYDRO 1,4 DIAZEPIN 6 YL] 1H INDAZOLE 3 CARBOXAMIDE; PROPYLAMINE; SEROTONIN 3 ANTAGONIST; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032480377     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00616-4     Document Type: Article

References (10)

1. 1. Part 1: Harada, H.; Morie, T.; Kato, S. Chem. Pharm. Bull. 1998, in press.
2. 2. Yoshida, N.; Omoya, H.; Kato, S.; Ito, T. Eur. J. Pharmacol. 1992, 216, 435-440.
3. 3 Receptor Antagonists. In 5-Hydroxytryptamine-3 Receptor Antagonists. King, F. D.; Jones, B. J.; Sanger, G. J. Eds., CRC Press Inc., 1994; pp. 1-43.
4. 4. Kato, S.; Morie, T.; Ito, T.; Yoshida, N. Jpn. Kokai Tokkyo Koho JP 05,230,057 [93,230,57] [Chem. Abstr., 1994, 120, 164242c].
5. 5. Harada, H.; Morie, T.; Kato, S. Tetrahedron: Asymmetry 1997, 8, 2367-2374.
6. 6. Willems, J. G. H.; Hersmis, M. C.; Gelder, R.; Smits, J. M. M.; Hammink, J. B.; Dommerholt, F. J.; Thijs L.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1997, 963-967.
7. 7. Kato, S.; Harada, H.; Morie, T. J. Chem. Soc., Perkin Trans, 1 1997, 3219-3225.
8. 8. Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619.
9. 9. Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073-4076.
10. 10. The pure carboxamide (R)-1 was obtained by several crystallizations of the crystals which were prepared from the crude amine 2 without column chromatography.