Practical and large-scale synthesis of rac-(3S,4aR,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g] quinoline-3-carboxylic acid methyl Ester

Organic Process Research and Development

Volumn 4, Issue 6, 2000, Pages 460-466

  Bänziger, Markus ^a   Cercus, Jacques ^a   Stampfer, Wolfgang ^a   Sunay, Ustun ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034345879     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0000531     Document Type: Article

References (26)

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2. Berde, B.; Stürmer, E. In Ergot Alkaloids and Related Compounds; Schield, H. B., Ed.; Springer Press: Berlin/Heidelberg/New York, 1978. Schardt, F.; Miskra, R. B. Ther. Ggw. 1982, 121, 26.
3. Nordmann, R.; Petcher. T. J. J. Med. Chem. 1985, 28, 367.
4. All compounds drawn with stereobonds are racemic!
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13. Baenziger, M.; Mak, C.-P.; Muehle, H.; Nobs, F.; Prikoszovich, W.; Reber, J.-L.; Sunay, U. Org. Process Res. Dev. 1997, 1, 395-406.
14. Mellin, C.; Hacksell, U. Tetrahedron 1987, 43, 5443.
15. Johansson, A. M.; Mellin, C.; Hacksell, U. J. Org. Chem. 1986, 51, 5252. Barnes, R. A.; Bush, W. M. J. Am. Chem. Soc. 1959, 81, 4705. Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930.
16. Johansson, A. M.; Mellin, C.; Hacksell, U. J. Org. Chem. 1986, 51, 5252. Barnes, R. A.; Bush, W. M. J. Am. Chem. Soc. 1959, 81, 4705. Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930.
17. Johansson, A. M.; Mellin, C.; Hacksell, U. J. Org. Chem. 1986, 51, 5252. Barnes, R. A.; Bush, W. M. J. Am. Chem. Soc. 1959, 81, 4705. Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930.
18. For hydrogenation of similar systems see: Lee, J.; Gauthier, D.; Rivero, R. A. J. Org. Chem. 1999, 64, 3060. Pollack. M. A. J. Am.Chem. Soc. 1943, 65, 1335.
19. For hydrogenation of similar systems see: Lee, J.; Gauthier, D.; Rivero, R. A. J. Org. Chem. 1999, 64, 3060. Pollack. M. A. J. Am.Chem. Soc. 1943, 65, 1335.
20. The ammonia was distilled from steel cylinders, also in plant scale, to prevent the introduction of iron impurities, which can catalyze the decomposition reaction of lithium with ammonia or tert-butyl alcohol; Harvey, R. G. J. Org. Chem. 1967, 32, 238; Harvey, R. G.; Urberg, K. J. Org. Chem. 1968, 33, 2570; Harvey, R. G. Synthesis 1970, 161.
21. The ammonia was distilled from steel cylinders, also in plant scale, to prevent the introduction of iron impurities, which can catalyze the decomposition reaction of lithium with ammonia or tert-butyl alcohol; Harvey, R. G. J. Org. Chem. 1967, 32, 238; Harvey, R. G.; Urberg, K. J. Org. Chem. 1968, 33, 2570; Harvey, R. G. Synthesis 1970, 161.
22. The ammonia was distilled from steel cylinders, also in plant scale, to prevent the introduction of iron impurities, which can catalyze the decomposition reaction of lithium with ammonia or tert-butyl alcohol; Harvey, R. G. J. Org. Chem. 1967, 32, 238; Harvey, R. G.; Urberg, K. J. Org. Chem. 1968, 33, 2570; Harvey, R. G. Synthesis 1970, 161.
23. For Birch reduction in similar solvent systems, see: Dryden, H. L.; Webber, G. M.; Burtner, R R.; Cella, J. A. J. Org. Chem. 1961, 26, 3237; Donaldson, R. E.; Fuchs, P. L. J. Org. Chem. 1977, 42, 2032.
24. For Birch reduction in similar solvent systems, see: Dryden, H. L.; Webber, G. M.; Burtner, R R.; Cella, J. A. J. Org. Chem. 1961, 26, 3237; Donaldson, R. E.; Fuchs, P. L. J. Org. Chem. 1977, 42, 2032.
25. Spaar, R.; Suter, G. A simplified Hazard Analysis Scheme for Use in Process Development. Presented at the 7th International Symposium on Loss Prevention and Safety Production in the Process Industry, Taorimina, Italy, May 4-8, 1992.
26. Rabideau, P. W. Tetrahedron 1989, 45, 1579; Recommendation of CHE-METALL in their brochure "Lithium Metal Properties and Applications" to work under argon, when using lithium metal.