derivatization of a racemic

[eer]

Hi,

I am a chemical pharmacologist of Barcelona. My research is about neurotoxicity of amphetamine derivatives.

I have to synthesize a pure enantiomer of an amphetamine derivative (R (-) MDMA), which has no psychoactive activity. However it is important to study its involvement in some neurotoxic lesions. To isolate it from the (+/-) MDMA it must be derivatized with 1(9-fluorenyl)ethyl need chloroformate solution but this reagent is very expensive. In sigma Aldrich the cost is 793 € for 10 ml and I need about 30-40 ml. Anyone have any idea if I can use any similar reagent more affordable? or how do I get the reagent at a reasonable price?

Thank you

[Tartaglia]

I would look to see if there are any chiral 3,4 dihydroxy amphetamine like natural products available and then you won't have to resolve but can build the methylene five membered ring in after

 

By the way, I expect this post will get some attention from the moderators - for my penny's worth, you look too credible to be doing something dodgy!

[John Cuthber]

Have you thought about preparative scale HPLC?

It would be expensive to set up, but once you get it working you can use it for MDMA and also for any further similar work you do.

 

BTW, what do you plan to do with the other isomer?

[UC]

Why not utilize the old-as-dirt separation of isomers by crystallization with enantiomerically pure tartaric acid or other suitable chiral resolving compound? One of the salts should be significantly less soluble than the other. I did this in a freshman-level organic chemistry class with 1-phenethylamine and it works quite well.

 

Clearly you don't need something of preparative scale. Recovery won't be 100% of the desired isomer, but it should be quite a bit cheaper than whatever method you wanted to use.

 

Also, http://www.springerlink.com/content/j41636h201010558/ suggests that both isomers do have activity.

[Blakelyneal]

Are you able to use some type of biological process to separate the two?

 

that would seem easier