05-10-01 18:55
No 193407
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.
(Chief Bee)
05-10-01 19:33
No 193420
A birch reduction on tryptophan would destroy the indole ring, unfortunately.
http://rhodium.lycaeum.org
(Hive Bee)
05-14-01 20:18
No 194488
If one used the Kalium or Natrium route would it be then.
(Chief Bee)
05-15-01 05:24
No 194573
I believe any birch-like reduction would destroy the indole ring.
http://rhodium.lycaeum.org
(Hive Bee)
05-15-01 14:07
No 194669
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...
(Hive Bee / Eraser)
05-16-01 03:51
No 194853
What about Pt/C a la what KrZ did with phenylalanine ?
e109
(Hive Addict)
05-16-01 19:43
No 194968
What about Pt/C a la what KrZ did with phenylalanine ?
Perhaps it would work as well as it does with phenylalanine.
(Hive Addict)
05-16-01 19:46
No 194969
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
(Chief Bee)
05-16-01 20:15
No 194979
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
(Stranger)
05-17-01 04:01
No 195058
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.
(Hive Bee)
05-17-01 10:42
No 195146
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.
(Hallucinogenius)
05-19-01 08:47
No 195638
Birch kiddies take their first tentative steps into tryptamines. Result: TOTAL DISASTER.
(Hive Bee)
05-19-01 11:41
No 195654
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.