Your views on synthesis of tryptamine or alpha- methyltryptamine (AMT) from indole-3-aldehyde

[xoxo2.0]

Hello members, i was recently interested in synthesis of AMT and the easiest way i think is from indole-3-aldehyde (made from vilsmeier haack) by henry reaction followed by reductive ammonolysis.

So the thing is i was wondering that i could make tryptamine doing same, I just want to know your views on formation of beta-carbolines during reduction how much are they produced and tryptamine being pretty sensitive molecule might cyclize during reduction, currently to get tryptamine i decarboxylate tryptophan

 

[Swirly]

In fact I will try this one.

Indole-3-aldehyde you can buy. Henry reaction with nitroethane, then a NaBH4 + CuCl2 reduction, hydrogenation. A few unclear posts on The Vespiary write that it is possible but with low yields...

 

[xoxo2.0]

Yeah, possible for sure but yield for tryptamine are not reported (or i didn't find) in most of the well known forums, but found a paper which claims to have pretty good yields for tryptamine. (about 80%)

clearnet:

View of Three-Steps Synthesis of Tryptamine Derivatives from Indole-3-Carboxaldehyde