Issue 74, 2014
From the journal:

RSC Advances

Transition metal-catalyzed redox isomerization of codeine and morphine in water†

Antonio Bermejo Gómez,‡ab   Pär Holmberg,‡c   Jan-E. Bäckvall‡ab  and  Belén Martín-Matute‡*ab  

* Corresponding authors

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden
E-mail: belen@organ.su.se
Fax: +46 815 49 08

b Berzelii Center EXSELENT, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden
Fax: +46 815 49 08

c Cambrex Karlskoga AB, SE-691 85, Karlskoga, Sweden
E-mail: par.holmberg@cambrex.com
Fax: +46 586 78 3129

Abstract

A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)2]BF4 and 1,3,5-triaza-7-phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.

Graphical abstract: Transition metal-catalyzed redox isomerization of codeine and morphine in water

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Article information

DOI
https://doi.org/10.1039/C4RA07735K
Article type
Paper
Submitted
28 Jul 2014
Accepted
06 Aug 2014
First published
06 Aug 2014

RSC Adv., 2014,4, 39519-39522

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Transition metal-catalyzed redox isomerization of codeine and morphine in water

A. B. Gómez, P. Holmberg, Jan-E. Bäckvall and B. Martín-Matute, RSC Adv., 2014, 4, 39519 DOI: 10.1039/C4RA07735K

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