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Author: Subject: revised question of leuckart reaction
madscience
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[*] posted on 19-7-2016 at 14:31
revised question of leuckart reaction


Would the salt of formic acid work in the leuckart reaction like sodium formate and potassium formate, and would it reduce the imine if you react aldehyde or ketone with a amine with formate salt as the reducing agent and would still form the n formyl impurities
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[*] posted on 19-7-2016 at 15:45


Sodium formate is a salt of formic acid... I have difficulty parsing your question. It is worded poorly, with low effort.

> would it reduce the imine [if you react aldehyde or ketone with a amine (the formate salt?)] with formate salt as the reducing agent

Yes, I think (formic anion can produce the hydride anion, which is pretty neat!) But only the ammonium or other quaternary amine salt!

> would still form the n formyl impurities

Well, amines ARE bases, and formic ACID is an ACID. What happens when base meets acid?

The formylation occurs (according to this: https://www.erowid.org/archive/rhodium/pdf/leuckart.pdf) when there is an excess of ammonium formate or formamide. I don't see why this is an issue for whatever you have planned for your P2P or whatnot because it should be butt easy to hydrolyze!

Please do some research of your own, and be aware I am only barely learning Org Chemistry.
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[*] posted on 19-7-2016 at 16:14


im trying to make alanine
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[*] posted on 19-7-2016 at 16:29


Why didn't you say so?

So, you want to reductively aminate pyruvic acid? Here is what googling gave me

https://aiche.confex.com/aiche/2008/techprogram/P131885.HTM
Check out the papers on the bottom of the page too

However, some other papers I read suggested that pyruvic acid does not give high yields.

Damn! Im spoonfeeding you :mad:

[Edited on 2016-7-20 by myristicinaldehyde]
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[*] posted on 19-7-2016 at 18:25


Quote: Originally posted by myristicinaldehyde  

However, some other papers I read suggested that pyruvic acid does not give high yields.

[Edited on 2016-7-20 by myristicinaldehyde]


I'm surprised any significant yield could be obtained, due to the presence of the other C=O group that you have to avoid aminating. Although I guess it is part of the carboxyl group, which could promote selectivity toward the other ketone if you wanted. Interesting.




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[*] posted on 20-7-2016 at 05:27


The paper was dealing with borohydride-promoted amination of aliphatic ketones, with the low yield as a note. I don't think amination of a carboxylic acid group is possible- but it must be doing something to prevent proper yield of the alanine.
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[*] posted on 20-7-2016 at 16:26


then how the industry make alanine you can buy it from suppliers different kind of amino acids
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[*] posted on 20-7-2016 at 23:26


Quote: Originally posted by madscience  
then how the industry make alanine you can buy it from suppliers different kind of amino acids

This is a common route:

https://en.wikipedia.org/wiki/Strecker_amino_acid_synthesis

Alanine could be made from ethanol (after oxidizing it to acetaldehyde) and an alkali cyanide salt.

[Edited on 7/21/16 by Melgar]
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[*] posted on 21-7-2016 at 05:16


Industrially, L-alanine is made biosynthetically.



As below, so above.
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[*] posted on 21-7-2016 at 07:38


Which optical stereoisomer are you looking to make? In case you're not familiar with optical isomers, we're talking about d-alanine vs l-alanine. The traditional Strecker synthesis yields a racemic mixture of the product's optical isomers, but it can be modified to be stereoselective.

[Edited on 21-7-2016 by CRUSTY]




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[*] posted on 21-7-2016 at 10:21


L alanine
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[*] posted on 21-7-2016 at 19:31


Quote: Originally posted by madscience  
L alanine


Okay. In that case, I'm not sure how stereoselective or isomerically preferential this is, but for a somewhat easier synthesis, you could try the ammonolysis of 2-bromopropanoic acid, which would most likely yield a racemic mixture depending on the reaction conditions, which you could then purify the l- isomer via whatever sort of chiral resolution works for you.




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