Opylation
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Possible 2-(dimethylamino)propan-1-ol synthesis via DMAE
Hello everyone,
So I am curious as to whether or not it would be possible to Synthesize 2-(dimethylamino)propan-1-ol by oxidizing DMAE (Dimethylethanolamine) to the
carboxylic acid derivative and then perform an enolate ion methylation to get alpha-methyldimethylaminoacetic acid. Then at this point reduce the
carboxylic acid back to an alcohol to produce alpha-methyldimethylaminoethanol? Or would it be more feasible to do something with serine?
Pic 1: DMAE
Pic 2: Serine
[Edited on 31-8-2019 by Opylation]
 
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Boffis
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Hi Opylation reducing carboxylic acids to alcohol is difficult in an amateur setting. Could you start from 1,3-propanediol via 3 bromopropanol then
react it with dimethylamine?
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Pumukli
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That would be a different compound!
Why not start from 1,2-prpanediol, selectively oxidise the secondary -OH to =O, then reductive amination with dimethylamine?
The workup may not be easy.
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Boffis
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Ah Yes. You are right pumukli but 1,2-propanediol is much easier to get.
So my question remains the same.
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CuReUS
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Quote: Originally posted by Opylation  | | So I am curious as to whether or not it would be possible to Synthesize 2-(dimethylamino)propan-1-ol by oxidizing DMAE (Dimethylethanolamine) to the
carboxylic acid derivative and then perform an enolate ion methylation to get alpha-methyldimethylaminoacetic acid |
You would end up with a quaternary ammonium compound instead | Quote: | | Or would it be more feasible to do something with serine? |
In that case,you would have to reduce the COOH to
alkane (which is hard) without affecting the OH(which you would have to protect and deprotect,further complicating the reaction).
The best way is to dimethylate alanine followed by a bouveault-blanc reduction
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Opylation
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Thank you all for the responses
CuReUs, I’m not following you, it looks like the bouveault-blanc reduction is for carbonyl groups where as aniline is an aryl amine
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