[TJGuitarZ]

Hey everyone,

I attend college at Kettering University. I am a chemistry major in an organic chemistry lab. We are doing a project on the synthesis of a drug -- in this case Prozac. I've spent approximately 8 hours searching online, but the only decent thing I have come up with is...

[url=http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00530

I tried searching google for "Synthesis of Fluoxetine," "Synthesis of 3-phenyl-3-[4-(trifluoromethyl)phenoxy]-propan-1-amine," and countless others. I've searched numerous patent numbers, but none leading me where I need to be.

In addition to explaining the synthesis, I need to give the percent yields for each step as well as the atmospheric conditions. Furthermore, my starting compound can have no more than 6 carbons.

Can someone give me some good sources to investigate? From the way my teacher described the project, it is basically a "get lucky" and stumble upon all the completed work on the internet. Unfortunately, I'm not getting lucky with Prozac.

Thanks for reading and all the future help.

-TJ-

Also, nice forums you got here. I'm falling more and more in love with Chemistry, so you might see me around here more often.

[agrobert]

Try using Google Scholar to do your searches through your university proxy or an on campus computer.  Your school should have some access to articles in ACS journals as well as Tetrahedron.

scholar.google.com

I would link articles but I don't know what you have access to.

[TJGuitarZ]

WOW! That helped a lot! I actually think I found something that lays it all out for me, though it will take time to sort through all the complex chemistry to get at what it is saying. With your knowledge, does the following link seem to explain and outline the synthesis for prozac (Fluoxetine)?
http://www.google.com/patents?hl=en&lr=&vid=USPAT6028224&id=KSkDAAAAEBAJ&oi=fnd&dq=synthesis+of+fluoxetine

Thanks again, agrobert, you really helped me out.

[Borek]

What I don't get is why did you use Google for such a research in the first place. There are specialized services that allow to search through chemical literature, ask in your library.

[TJGuitarZ]

I've never done this kind of research before. I'm not too sure if my library even has that kind of database. I guess I plead ignorance. 

[agrobert]

Borek is right there are better databases for research.  Check out your school library and see if they offer seminars on using the chemistry library and online databases.  Google Scholar is quick and easy to use because it usually links you to the article if you have access but it is limited.  Good databases will search CAS numbers and chemical structures.  Check out Beilstein and SciFinder Scholar for CAS registry searches and structure/reactions.  Your university website should have links in the Science department for electronic journals and other search engines like Web of Science.

The patent you found looks good but I would suggest finding the original research synthesis of Prozac as well as other routes for comparison.  Often patents are modifications of existing syntheses with improvement or novel reactions.  Check the references in the patent.

[TJGuitarZ]

Well, I guess I wasted my time on google. I found out today that I have quite a few research databases to go to at the library. I found a new synthesis that I mostly understand and is more outlined for me.

http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6THS-447D8S2-4-3&_cdi=5290&_user=915064&_orig=search&_coverDate=12%2F17%2F2001&_sk=999579948&view=c&wchp=dGLzVzz-zSkzk&md5=a9a9735b0cdf7d42c7cc54c4e5e51959&ie=/sdarticle.pdf

My new problem is that methyl-4-oxo-4-phenylbutanoate, the starting chemical in that synthesis, has too many carbons as outlined by my rubric. I am limited to 6 for my starting product. I was thinking of combining a bromobenzene with methyl-4-oxobutanoate, but I don't know how that would turn out, nor the atmospheric conditions necessary, nor the percent yield. Any advice?

[Borek]

Searche these databases for methyl-4-oxo-4-phenylbutanoate synthesis?

[AWK]

http://voh.chem.ucla.edu/vohtar/spring01/130B/pdf/soln.doc

See: Lednicer book on drug synthesis

[TJGuitarZ]

Hmm... I searched the databases but it had nothing.

AWK, I looked through that document, but I'm not sure what I am looking at.

[AWK]

Page 12

[TJGuitarZ]

Oh! I didn't look hard enough.

I really like the synthesis that starts with 4-Trifluoromethylfluorobenzene, however I need the percent yields and atmospheric conditions of each reaction. He gave a note that it was found in section 21.3 of one of the two books at the beginning of the document. Would I be able to find those books online?

[Tijana]

Just the topic I was looking for!

I also have a project to go through the synthesis of prozac, and when I found all this, it really helped me a lot! Thanks guys!