mercredi 4 juillet 2007

Synthesis of 2-methyltryptamine

As some people probably noticed, I like OPRD (Organic Process Research & Development), of course chemically speaking nothing weird, only classic chemistry but scalable synthesis and no COLUMN, for me the dream.
And sometimes we can find very interesting stuff, as this synthesis of the 2-methyltryptamine by the Grandberg methodology, which is indeed a modified Fisher indole synthesis.
This chemistry starts with the formation of the hydrazone between the phenylhydrazine and the 5-chloropentan-2-one, after cyclization and isomerization from iminium to enamine form, the rearrangment takes place to afford the tricyclic intermediates, which after loss of a proton provides the 2-methyltryptamine with 42% in almost 20 Kg scale!!!!! in A 800L reactor!!!!!!!!!!

Optimization and Scale-Up of the Grandberg Synthesis of 2-Methyltryptamine
Joel Slade, David Parker, Michael Girgis, Raeann Wu, Scott Joseph, and Oljan Repi
OPRD, 2007

44 commentaires:

milkshake a dit…

this is a lovely paper, I have noticed it too.

Org Process R&D is my favorite journal, the procedures there usualy work (even when scaled down by factor of 1:10000 :)

Georges D a dit…

it 's a very nice abstract. But what about a small account on molecular recognitions, nadh models or wald disney chemistry such as porphyrin associated with acetylenic bulding blocks??

Francois T a dit…

Do you think that it iw possible to metalate this compounds' familly in diethyl ether ?

HetChem a dit…

Dear Georges d, francois t and nelly p.

Or Maybe it's Thomas P, Nicolas L and Pierre B. I don't know...
Don't polute my blog please.
Otherwise I will send you "la famiglia", and no holiday in Italy...

Anonyme a dit…

I have to do it with an carboxyl group on the top of the benzene hydrazine, do you think it will work the same?

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