4-methoxy indole to 4-ho-dmt

[blunts]

swim was wondering if its possible/feasable to get some psilocybin from 4-meo-indole.  sorry swim doesnt have too much chemistry experience (classes start in a few weeks )  any help or info would be appreciated

[Rhodium]

I think 4-MeO-Indole derivatives can be demethylated using buffered boron tribromide, but I'm not sure. I can say as much as it is not an easy transformation.

[blunts]

anyone know what else 4-methoxy indole could be used as a precursor for?

[Rhodium]

Any 4-Methoxy-tryptamine, such as

4-MeO-MIPT

(http://www.erowid.org/library/books_online/tihkal/tihkal39.shtml)

[pHarmacist]

swim was wondering if its possible/feasable to get some psilocybin from 4-meo-indole.

There is an old route to Serotonin where they preform de-O-methylation using AlCl3. For experimental details turn your attention to:

Abramovich, R. A and Shapiro, D., J. Chem. Soc., 1956, 4589; Henecka, H., Timmler, H., Lorenz, R., and Geiger, W., Chem.Ber., 1957, 90, 1060

I can't see why they start with p-methoxy-phenylhydrazone, a number of other counterparts that are easier to get rid of would give better yield in the last step..

[Rhodium]

What O-protection groups (avaliable in the fifties), which also survives the initial aniline diazotization to the phenylhydrazine, followed by the Fischer Indole Synthesis, can you think of?

There is always benzyl, but maybe they didn't have access to high-pressure catalytic hydrogenation in that lab (CTH wasn't invented yet).

[Rhodium]

Well, the first Catalytic Transfer Hydrogenation was reported in the literature only 50 years ago:

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">"In 1952, Braude, Linstead, et al. reported the striking discovery that ethylenic
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">and acetylenic linkages could be reduced in high yield and purity by refluxing with
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">cyclohexene in tetrahydrofuran at 65°C in the presence of palladium black."

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">"[They] made the suggestion that catalytic hydrogen transfer from an organic
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">donor molecule to a variety of organic acceptors might be possible under mild
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">conditions. In fact, sporadic use had been made in the past of unsaturated
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">compounds as hydrogen acceptors in catalytic dehydrogenation reactions.
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">However, few systematic studies were directed toward the reverse process,
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453254-file_fdlo.gif" title="View this image">catalytic transfer hydrogenation."

Cited from:

Catalytic Transfer Hydrogenation (Review)
Gottfried Brieger, Terry J. Nestrick

Chem. Rev. 74, 567-580 (1974)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/cth.review.pdf)

Edit: Hmm, it seems like the question I answered disappeared meanwhile... Oh well, it doesn't matter, this is interesting anyway  

Also, here is a related review article of interest:

Heterogeneous Catalytic Transfer Hydrogenation (Review)
R.A.W. Johnstone, A.H. Wilby, I.D. Entwistle

Chem. Rev. 85, 129-170 (1985)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/heterogenous.cth.review.pdf)

[pHarmacist]

Thanks for the info. I deleted my post as I thought no one would answer my question...

EDIT: The question was: "Oh, no kidding, so when did CTH came about?"

[pHarmacist]

See the last step (Scheme 1):

Post 456207

(pHarmacist: "Labelled indolealkylamines for brain mapping", Tryptamine Chemistry)

Good luck!