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synthesis of DMT from IAA

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somuchclass:
I once read at "DMT World" something to the effect that the IAA + LAH-->PBr3-->NH(CH3)2 in DMSO or sulfolane (polar, aprotic solvents) is one of the oldest methods for producing DMT. 

The reason that the last reaction doesn't work well with bromosafrole is that in that case you are dealing with a secondary carbon (although I wonder if anyone has tried applying Shulgin's sulfolane/methylone method to bromosafrole; after all, the original German patent for MDMA used bromosafrole so it must not be impossible). 

In the case of DMT, the carbon to which the bromine is attached is primary and yields should be much better than with MDMA because there is less steric hindrance.

Of course, the easiest method is probably to simply extract the DMT from Mimosa hostilis bark.

phenethyl_man:
Yes, I plan do it this way, except for avoiding the use of LAH by using either NaBH4/I2 in THF [1], or by forming an ester which can be reduced w/NaBH4/AlCl3 in diglyme [2].


[1] Selective reduction of carboxylic acids into alcohols using sodium borohydride and iodine
J. V. Bhaskar Kanth, Mariappan Periasamy;
J. Org. Chem.; 1991; 56(20); 5964-5965.

[2] REDUCTION OF ESTER AND OTHER DIFFICULTY REDUCIBLE GROUPS BY SODIUM BOROHYDRIDE
Herbert C. Brown, B. C. Subba Rao;
J. Am. Chem. Soc.; 1955; 77(11); 3164-3164.

Lilienthal:
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.

phenethyl_man:
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.
--- End quote ---


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...

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