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

 

[Swirly]

Thanks for posting the paper. This is a great find. Well it seems that it works well to make tryptamine. Yes, aMT would be the same synth as in the paper, but just replace nitromethane with nitroethane. Guess we have to try. But do the nickel salts have any advantage over copper salts?

Still I think to make tryptamine this way is more difficult than from tryptophan.

Beta-carbolines? Don't you need an aldehyde or something for those to form? Are those not formed when reacting tryptamine not in the formation of tryptamine?