Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 2. l-homophenylalanine-based syntheses

Organic Process Research and Development

Volumn 2, Issue 3, 1998, Pages 186-193

  Draper, Richard W ^a   Hou, Donald ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032344940     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op970122k     Document Type: Article

References (6)

1. See preceding paper and references therein for an introduction to the pharmacology of 1 and a discussion on alternative synthetic approaches: Draper, R. W.; Hou, D.; Iyer, R.; Lee, G. M.; Liang, J. T.; Mas, J. L.; Tormos, W.; Vater, E. J.; Günter, F.; Mergelsberg, I.; Scherer, D. Org. Process Res. Dev. 1998, 2, 175.
2. (+)-L-Homophenylalanine is available in bulk quantities from Tanabe U.S.A., Inc., and Aceto Corporation (U.S. Representative for Ajinomoto).
3. (a) Norlander, E. J.; Payne, M. J.; Njoroge, F. G.; Vishwanath, V. M.; Han, G. R.; Laikos, G. D.; Balk, M. A. J. Org. Chem. 1985, 50, 3619.
4. (b) Buckley, T. F., III; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157.
5. McClure, D. E.; Lumma, P. K.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1983, 48, 2675.
6. Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630.