Question about the Synthesis of alpha-methyltryptamine using tryptophan

[bigdigrandy]

I have an Idea of a possible Synthesis route of aMT using tryptophan as the starting material.
I have looked for a synthesis like this on this forum, but I have not found anything, so if a question like this already exists I am very sorry.

The synthesis i thought of is starting with the reduction of the carboxyl groupe of tryptophan using LAH, to get an hydroxy group, and then using hydrogen iodide in the presence of red phosphorus to remove the hydroxy group and turn it into tryptamine iodide.

The tryptamine iodide would now be reduced by Lithiumaluminiumhydride to give the final product aMT

My Question now is if this synthesis would theoretically work, and what would be the ideal solvent to perform this synthesis in?
If this synthesis works aMT could be made by easily available and non suspicious recurses, which could be made with minimal equipment and knowledge.
It would be great if somebody could help me, because my chemistry skills are not really good and I do not trust myself to try this one without asking somebody if it would even work.

 

[HerrHaber]

Well there are several weak points in your plan but hey, congrats for such a daring synthetic pathway plan. First of all I kindly recommend using Red-Al (long name you should check it out for yourself) it's much less pyrophoric so safer to handle. Second thing is that you will need the methyl ester of Trp and I have some previous work done meaning I can supply you with a convenient method to prepare it, that with LAH or Red-Al would afford the hydroxymethyl analog. As for red P/HI I would expect it to be reduced to AMT if you're lucky (idk if this works for primary in a similar manner as for secondary alcohols so you need to check). I'm pretty confident that there are more convenient iodination methods and Iodine is a good enough leaving group that you only need to put it together with a molecule that he would rather be on than on the Trp. Another thing to consider is that tryptamine chemistry is pretty tedious and invariably frustrating even if by luck just a tiny bit.