Also, would it be possible to simply reduce the acid to tryptophol, react tryptophol with an acid halide to displace the hydroxyl with a halogen, followed by aminolysis w/dimethylamine to displace the halogen and form the amine.
Im quite sure this synth s on rhodium site.
My personal eksp. with it was a bit low yeald (50-60%)
I'ts some years ago, and there are (ofcourse) no rekord of the eksperiment, so you have to stick with it.
The route from IAA works greath, nice xtaline (with sometimes is hard) product.
The oxalylchloride route is also quite easy to work with, depending on wath's kind of chemicals you have on hand.
And dont bee impatient with chemistry. It is one of those think that takse the time it want's (oposite sex)
Post 527262 (https://www.thevespiary.org/talk/index.php?topic=9415.msg52726200#msg52726200)
(n00dle: "LSD vs peptide coupling", Tryptamine Chemistry).NaBH4 / I2 might reduce the indole ring system to an indoline system by reduction of the 2,3-bond. Better check the literature and/or check by TLC. Indolines are slightly basic aniline analogs and have a yellow Ehrlich color reaction.
The NaBH4/I2 system can reduce double bonds? If so this rxn might be more useful than I thought. Do you have any evidence of this? Perhaps cinnamic acid could be reduced directly to 3-phenylpropanol. I wonder if iodine enhances the reduction potential of borohydride in alcoholic solvents as well...