Synthesizing psilocin or 4-Ace-DMT from 5-MeO-Tryptamine

[actualdisso]

A beginner here. I was wondering if it was possible to synthesize either psilocin or 4-Ace-DMT, starting with 5-Meo-Tryptamine. I'm very confused as to how to create the hydroxyl group of the psilocin's ring from the starting molecule (see the attached image).

Am I supposed to use a redox reaction on 5-MeO and then rebuild the OH side chain somehow? Any help is appreciated, thanks!

 

[HerrHaber]

Just to be feasible I would personally start with either 4-OH tryptamine or 4-acetoxy tryptamine (prefered so that you don't methylate the OH by accident, even though reductive amination with formaldehyde isn't a concearn, but more the acidity of the 4-hydroxyl which is partially phenolic in nature), another experimented route is from 4-OH or 4-acetoxy indole and oxalyl chloride (classical, tedious and not beginner friendly), Fisher indole synthesis with 3-acetoxy phenylhydrazine (if you can find it available) and the expensive N,N-dimethylamino-n-butyl-diethylacetal might be also possible and more elegant. Indole and especially tryptamine chemistry is often frustrating and I speak from experience in research setting.

 

[Joker_55555]

A beginner here. I was wondering if it was possible to synthesize either psilocin or 4-Ace-DMT, starting with 5-Meo-Tryptamine. I'm very confused as to how to create the hydroxyl group of the psilocin's ring from the starting molecule (see the attached image).

Am I supposed to use a redox reaction on 5-MeO and then rebuild the OH side chain somehow? Any help is appreciated, thanks!

actualdissoNo, it is not possible to get from 5-Meo-dmt to 4-Ace-DMT.

 

[HerrHaber]

No, it is not possible to get from 5-Meo-dmt to 4-Ace-DMT.

Joker_333you must have noticed me how I avoided putting this traight (isn't impossible but would be a waste of tons of precursors and years of work to just prove in an analytical sense).

 

[Joker_55555]

you must have noticed me how I avoided putting this traight (isn't impossible but would be a waste of tons of precursors and years of work to just prove in an analytical sense).

HerrHaberThat's why I say it can't be built