Microwave-promoted acid-catalyzed rearrangement of morphinans - A high-yield synthesis of R(-)-apomorphine

Synthetic Communications

Volumn 38, Issue 6, 2008, Pages 866-872

  Csutoras C ^a   Berenyi S ^b   Neumeyer, J L ^c  

^a ESZTERHÁZY KÁROLY UNIVERSITY   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c MCLEAN HOSPITAL   (United States)

Author keywords

Acid catalyzed rearrangement; Apomorphine; Aporphines; Microwave synthesis; Morphinans; Morphine

Indexed keywords

APOMORPHINE; MORPHINAN DERIVATIVE; MORPHINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 39749122580     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701845357     Document Type: Article

References (10)

1. Matthiessen, A.; Wright, C. R. A. Monatsbericht: Organische Chemie: Apomorphin von Matthiessen und Wright. Arc. Pharm. 1870, 191 (2), 175.
2. Folkers, K. The preparation of pure apocodeine and its hydrochloride. J. Am. Chem. Soc. 1936, 58, 1814.
3. Small, L.; Faris, B. F.; Mallonee, J. E. The halogeno-morphides and -codides, and the mechanism of the morphine-apomorphine transformation. J. Org. Chem. 1940, 5, 334.
4. Granchelli, F. E.; Filer, C. N.; Soloway, A. H.; Neumeyer, J. L. Mechanistic aspects of the rearrangement of thebaine and codeine analogues in methanesulfonic acid. Improved method for synthesis of N-alkylated aporphines. J. Org. Chem. 1980, 45 (12), 2275.
5. Berényi, S.; Czirják, M.; Makleit, S. Rearrangement of morphinandienes in methanesulfonic acid. J. Chem. Soc., Perkin Trans. 1 1993, 2137.
6. Csutorás, C.; Berényi, S.; Neumeyer, J. L. Investigation of the acid-catalyzed rearrangement of morphinans. Lett. Org. Chem. 2007, 4, 409.
7. Zhang, A.; Neumeyer, J. L. Microwave-promoted Pd-catalyzed cyanation of aryl triflates: A fast and versatile access to 3-cyano-3-desoxy-10- ketomorphinans. Org. Lett. 2003, 5 (2), 201.
8. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - a review. Tetrahedron 2001, 57, 9225.
9. Larhed, M.; Moberg, C.; Hallberg, A. Microwave-accelerated homogeneous catalysis in organic chemistry. Acc. Chem. Res. 2002, 35, 717.
10. Atkinson, E. R.; Bullock, F. J.; Granchelli, F. E.; Archer, S.; Rosenberg, F. J.; Teiger, D. G.; Nachod, F. C. Emetic activity of N-substituted norapomorphines. J. Med. Chem. 1975, 18, 1000.