Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH12463
RESEARCH FRONT
Contents Vol 66(2)

A Multi-Step Continuous Flow Process for the N-Demethylation of Alkaloids

Yuji Nakano A , G. Paul Savage A , Simon Saubern A , Peter J. Scammells B and Anastasios Polyzos A C
+ Author Affiliations
- Author Affiliations

A CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic. 3169, Australia.

B Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Vic. 3052, Australia.

C Corresponding author. Email: tash.polyzos@csiro.au

Australian Journal of Chemistry 66(2) 178-182 https://doi.org/10.1071/CH12463
Submitted: 9 October 2012  Accepted: 13 November 2012   Published: 29 November 2012

Abstract

Dextromethorphan was N-demethylated using the non-classical Polonovski reaction under continuous flow conditions, in two steps: initial N-oxidation with m-chloroperbenzoic acid followed by iron-catalysed N-demethylation of the resulting N-oxide.


References

[1]  S. Thavaneswaran, K. McCamley, P. J. Scammells, Nat. Prod. Commun. 2006, 1, 885.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXit1eltA%3D%3D&md5=23f00672f325857e7d984902096ff057CAS |

[2]  J. V. Braun, Ber. Dtsch. Chem. Ges. 1909, 42, 2035.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  K. C. Rice, J. Org. Chem. 1975, 40, 1850.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXksVemt78%3D&md5=20c9563b539e6ff7958433d16a9d6a74CAS |

[4]  L. S. Schwab, J. Med. Chem. 1980, 23, 698.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXktF2isrw%3D&md5=6f068743bf27fb7bb1b9e1b6b1b5e5b7CAS |

[5]  J. A. Ripper, E. R. T. Tiekink, P. J. Scammells, Bioorg. Med. Chem. Lett. 2001, 11, 443.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhslOgurY%3D&md5=d13bddc703a91c021eede1a0284a0213CAS |

[6]  L. C. Portis, J. T. Klug, C. K. Mann, J. Org. Chem. 1974, 39, 3488.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  K. M. Madyastha, G. V. B. Reddy, J. Chem. Soc., Perkin Trans. 1 1994, 911.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXktlGqsb4%3D&md5=99aae615bfc269e3d45e16f605846c11CAS |

[8]  M. Polonovski, M. Polonovski, Bull. Soc. Chim. Fr. 1927, 41, 1190.

[9]  D. Grierson, in Organic Reactions (Ed. L. A. Paquette) 2004, pp. 85–295 (John Wiley & Sons, Inc.: Hoboken, NJ).

[10]  A. Mary, D. Z. Renko, C. Guillou, C. Thal, Tetrahedron Lett. 1997, 38, 5151.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXkvVChsLk%3D&md5=4f52c4272a0e55bab87dc77cc3001277CAS |

[11]  S. Han, J. Sweeney, E. Bachman, E. Schweiger, G. Forloni, J. Coyle, B. Davis, M. Joullié, Eur. J. Med. Chem. 1992, 27, 673.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXhsVOrsbY%3D&md5=f6e25c7e212755ec3e2bf42375a6e6abCAS |

[12]  K. McCamley, J. A. Ripper, R. D. Singer, P. J. Scammells, J. Org. Chem. 2003, 68, 9847.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXovVOitrw%3D&md5=51d4d520cff0659b655d9553afce8293CAS |

[13]  S. Thavaneswaran, P. J. Scammells, Bioorg. Med. Chem. Lett. 2006, 16, 2868.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjvFygsbk%3D&md5=b793a8304b5bf7a24baa18ecb612c0c8CAS |

[14]  Z. Dong, P. J. Scammells, J. Org. Chem. 2007, 72, 9881.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlWmurbO&md5=5adc03de28ef60877338cc491b1c263cCAS |

[15]  G. Kok, T. D. Ashton, P. J. Scammells, Adv. Synth. Catal. 2009, 351, 283.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvVWktLo%3D&md5=c5d7e6642bfdd54aefae69a70795a478CAS |

[16]  G. Kok, P. Scammells, Synthesis 2012, 44, 2587.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFaksLjO&md5=b010ebe0eff2a66a33a3d5df4f202ee8CAS |

[17]  G. B. Kok, C. C. Pye, R. D. Singer, P. J. Scammells, J. Org. Chem. 2010, 75, 4806.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnslCmt7Y%3D&md5=e4e4eb7612f98bb4868d3b3976a9f03bCAS |

[18]  G. B. Kok, P. J. Scammells, Bioorg. Med. Chem. Lett. 2010, 20, 4499.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptVSkt7c%3D&md5=3ef0f6dee97bce61261ced5d1ff2dfa5CAS |

[19]  G. B. Kok, P. J. Scammells, Org. Biomol. Chem. 2011, 9, 1008.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVCjtbk%3D&md5=7f55c7005c6b753afa4af6574f9b18d0CAS |

[20]  G. B. Kok, P. J. Scammells, Aust. J. Chem. 2011, 64, 1515.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVOqurfM&md5=b1739c78f457df498d057b103f58e750CAS |

[21]  A. Sipos, S. Berényi, Synlett 2008, 2008, 1703.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  S. Berényi, Z. Gyulai, A. Udvardy, A. Sipos, Tetrahedron Lett. 2010, 51, 1196.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  G. Singh, T. B. Koerner, S. B. Godefroy, C. Armand, Bioorg. Med. Chem. Lett. 2012, 22, 2160.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xis1Okt7k%3D&md5=0cabb9c23173167cba55e0efeb2c6f3fCAS |

[24]  X. Y. Mak, P. Laurino, P. H. Seeberger, Beilstein J. Org. Chem. 2009, 5, 19.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  C. Wiles, P. Watts, Eur. J. Org. Chem. 2008, 2008, 1655.
         | Crossref | GoogleScholarGoogle Scholar |

[26]  S. V. Ley, I. R. Baxendale, Chimia (Aarau) 2008, 62, 162.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltFGiu7c%3D&md5=2b1fe75e6f0e274c9c45e4fe163ffb84CAS |

[27]  I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby, G. K. Tranmer, Chem. Commun. 2006, 2566.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvV2gt7Y%3D&md5=531b92727344ec370e9d0727ed117ed4CAS |

[28]  A. Polyzos, M. O’Brien, T. P. Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. Int. Ed. 2011, 50, 1190.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFKgtbo%3D&md5=98708bb6d140ab1c30d2236e140b24d6CAS |

[29]  A. Palmieri, S. V. Ley, A. Polyzos, M. Ladlow, I. R. Baxendale, Beilstein J. Org. Chem. 2009, 5, 23.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  I. R. Baxendale, S. V. Ley, in New Avenues to Efficient Chemical Synthesis (Eds P. H. Seeberger, T. Blume) 2007, Vol. 2006/3, pp. 151–185 (Springer: Berlin).

[31]  M. Brasholz, B. A. Johnson, J. M. Macdonald, A. Polyzos, J. Tsanaktsidis, S. Saubern, A. B. Holmes, J. H. Ryan, Tetrahedron 2010, 66, 6445.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptlaqtr8%3D&md5=2c6f5f1198b56c170236ac1186f5466eCAS |

[32]  M. Brasholz, S. Saubern, G. P. Savage, Aust. J. Chem. 2011, 64, 1397.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlWjtLfN&md5=ba3b6b13370aace67b3a6bc3f55d0f66CAS |

[33]  A. McKillop, W. R. Sanderson, Tetrahedron 1995, 51, 6145.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlvFOhtb4%3D&md5=6e90a12ff195fbee36e0fee05d8550fdCAS |