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Autor Thema: 4-Chlorodehydromethyltestosterone Synthesis/patent  (Gelesen 4441 mal)

karpen

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4-Chlorodehydromethyltestosterone Synthesis/patent
« am: 17. Januar 2015, 12:16:26 »
Hello! I'm sorry that i don't write in German, but this is the only forum i feel comfortable in.

The thing is that I am a chemistry student, and i'm doing an essay for school.

For the school project, I need the synthesis of 4-Chlorodehydromethyltestosterone (Turinabol) which took place in 1961 by Jenapharm, and i have been searching the whole web to find it with no success at all.

Do anyone here have some litterature of it? It doesn't matter if it is in german or english.

Best regards, karpen


synthon

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Re: 4-Chlorodehydromethyltestosterone Synthesis/patent
« Antwort #1 am: 17. Januar 2015, 15:38:10 »
As a chemistry student (i.e. studying chemistry?) and/or via your school/university you should have access to scientific sources. Via these sources you can access the following papers:

- Background history in GDR: http://de.wikipedia.org/wiki/Staatsplanthema_14.25
- http://www.sciencedirect.com/science/article/pii/S0039128X99000033
- Manufacturer: http://de.wikipedia.org/wiki/Jenapharm
- using the CAS number 2446-23-3 you should be able to find additional sources
- seems to be available via China: http://www.lookchem.com/cas-244/2446-23-3.html
- Synthesis abstract and source: http://oasys2.confex.com/acs/233nm/techprogram/P1048604.HTM
- Some improvements have been made, as it looks like:
Zitat
The synthetic process of chlorodehydromethyltestosterone was improved. Chlorodehydromethyltestosterone was synthesized from methyltestosterone by cycloxidization with hydrogen peroxide to obtain cycloperoxene methyltestosterone, then subjected to chloridization with hydrochloric acid in presence of propanone to obtain chloromethyltestosterone which was further subjected to dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) using p-toluene sulfonic acid (PTS) as dehydrogenation catalyst in benzene. The overall yield was 30.0 %. Chem. structure of the product was confirmed by m.p., 1H-NMR and mass spectra. The synthetic route of this method is suitable for industrial prodn.
Source: Improved synthetic technology of chlorodehydromethyltestosterone
by Deng, Yan
Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United States, March 25-29, 2007, S.MEDI, 2007
- analytical profile is also available:
Zitat
Anal. data (GC, GC/MS, FTIR, HPLC, 1H- and 13C-NMR) for the anal. and identification of dehydrochlormethyltestosterone ((17β)-4-chloro-17-hydroxy-17-methylandrosta-1,4-dien-3-one) is presented. Historical background is also included.
Source: Dehydrochlormethyltestosterone: an analytical profile
by Wisniewski, Eric
Microgram Journal, 4(1-4):54, 2006

For copyright reasons I can't provide you with the protected papers, but you should be able to access the other stuff. A university bibliotheque should be a good source, here in Germany registration and access is usually free. Try and ask.

If you want just to synthesize it and use it "medically" - you most probably won't succeed. I dare say that someone who isn't able to find synthesis procedures on his own won't totally be able to synthesize such a molecule at all. But good luck with your school project! :)