Reduction of tryptophan to AMT, birch possibility?

[superhybrid]

I have not much research on the birch but am wondering if it can reduce the carboxylic acid functional group on trytophan to the corresponding methyl group.

Maybe a birch reduction can only be used to reduce benzylic hydroxyl groups.

[Rhodium]

A birch reduction on tryptophan would destroy the indole ring, unfortunately.

http://rhodium.lycaeum.org

[superhybrid]

If one used the Kalium or Natrium route would it be then.

[Rhodium]

I believe any birch-like reduction would destroy the indole ring.

http://rhodium.lycaeum.org

[jim]

MOst Birch reductions would. 

The Birch reduction would reduce the aromatic rings, but side reactions could occur that would then recreate the ring, like with an ephedrine reduction by Birch methods.

The likely hood of a Birch reduction being useful in this realm of chemistry is nominal. ANd the carboxyl group of tryptophan would not be effected...

[element109]

What about Pt/C a la what KrZ did with phenylalanine ?


e109

[terbium]

What about Pt/C a la what KrZ did with phenylalanine ?

Perhaps it would work as well as it does with phenylalanine.

[foxy2]

i have heard KRZ say that writeup was complete bullshit, but then again how can you tell?
To my knowledge it has never been verified.

Do Your Part To Win The War

[Rhodium]

That IS bullshit. There is only ONE known method of directly reducing a carboxylic acid group directly to a methyl, and that uses triethylsilane and tris(pentafluorophenyl)borane.

http://rhodium.lycaeum.org

[Helden]

Halo, my name is Helden:)
The Hundieker reaction may be of use to you here.
Reaction with ilver ions will convert the carboxyl gp to the corresponding salt. This is then reacted with bromine in TCM causing the pption AgBr - CO2. RBr is product.

[superhybrid]

Whatcha all mean? A carboxylic acid can be reduced to a alcohol with LAH and then from there...(chose yer reaction reduction)... That was one point I made earlier in a different post. Pd, Ni, yada yada.......... We are talking about a alpha methyl hydroxy group here. I don't think they are as big of a bitch to do something with over the benzylic hydroxyl. What about protecting the amine with a acetate and dehydrate with H2SO4 forming the alpha-(alkene) then birchit and then blamo you got yer stuff. I think the main purpose of a birch is to saturate a alkene. They work quite nice for that. Knowing that the aromaticity of a indole ring apparently is no match for even a Na or K solvated electron then possibly one would be destined to only use this method with a non-indole aromatic  I always thought aromaticity meant the ring was quite stable from attack but hey learn something new every day. We never did much study on indole compounds. Maybe when I take Org. III we will. Would be nice to know.

[KrZ]

Birch kiddies take their first tentative steps into tryptamines.  Result:  TOTAL DISASTER.  

[superhybrid]

Birch kiddies could really care less about tryptamines. That blasted carboxylic acid moiety is what swim would like to see gone and replaced with a methyl. Whether it be a phenylalanine reduced or L-dopa ester reacted with 2 moles NaH then combined with 1 mole DCM to form the methylene dioxy derivative then reduce the carboxylic acid to a methyl, there is some potential here. Tweaker delux one way or another.