The Hive > Tryptamine Chemistry

Suggested 2 step reaction to AMT

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Beard:

--- Quote from: Rhenium on April 04, 2000, 05:11:00 PM ---You can't reduce the group using standard methods, so how about these two papers which have definitely graced the Hive before...</p><p>1) Olah, G.A. et. al., J. Org. Chem., 44(8), 1979, pp 1247.</p><p>2) Sakai, T., et. al., Tet. Let., 28(33), 1987, pp 3817.</p><p>Both of these papers are different spins on Me3SiCl and NaI. The first turns the alcohol into a Iodide, and the second eliminates it all together. Both sets of reaction proceed at room temperature in good to excellant yield.
</p>

--- End quote ---

Referenced papers available here (no javascript required to download them):

* J. Org. Chem., Vol. 44 ( Issue 8 ), 1979, pp 1247. @ https://file.io/Cat32X or https://dropfile.to/oLDMK0S (24 hours)
* Tet. Let., Vol. 28 (Issue 33), 1987, pp 3817. @ https://file.io/hxGP7G or https://dropfile.to/JySchWf (24 hours)

Alts ( Javascript required, no SSL :( but always available ):
* http://www.xup.in/dl,58488579/J.org.chem1979%2844%291247.pdf/
* http://www.xup.in/dl,51447552/Tet._Let._1987_28(33)_pp3187.pdf/

I tried to upload them directly & attach to this post, but I kept getting an error:


--- Quote ---An Error Has Occurred!
Cannot access attachments upload path!
--- End quote ---

Tsathoggua:
How about conversion of the aliphatic -OH to the halide via a modified Appel rxn. This (Appel reaction) relies on conversion of PPh3 to a diphenylphosphonium halide, which is the active halogenation agent.

The classic rxn uses carbon tet and PPh3, which (the latter) can be used in catalytic quantities apparently. Yes toady once asked if chloroform could be used in place of carbon tet, for chlorinations, but seemingly whilst the reaction would proceed it would be exceedingly slow. It seems remarkably versatile, at least, inasmuch as one wishes to react an alcohol to an alkyl halide. The versatility comes from being able to utilize carbon tetrachloride, tetrabromide, tetraiodide (this last is thermodynamically unstable and should be stored if it must be so at 0'C or preferably, prepared and immediately cooled prior to use). It can be produced, reportedly via reaction of C-tet with I2, but MeI, I2, Br2 and even alkali metal ionic salts have been used for this modified Appel. It converts alcohols into alkyl halides. Quite a kick ass rxn. Been contemplating its use for synthesis of chlormethiazole or bromethiazole in fact, for times I've run out of SOCl2.

enone:
what about indole-3-acetic acid -> indole-3-acetone -> alpha-methyltryptamine?

IAA is sold in bulk all over. basically treat it like phenylacetic acid and distill the ketone from a mixture of it and lead (II) acetate, then run the leuckart with ammonium formate. really quick (and dirty) stuff, feasible for sure

micro:
Very interesting.
IAA is indeed quite available.

enone:
on second thought, maybe reductive amination with ammonium acetate and sodium cyanoborohydride wouldn't be the worst idea

https://anonimag.es/image/JJ7k

fixed link

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