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Author: Subject: Possible 2-(dimethylamino)propan-1-ol synthesis via DMAE
Opylation
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[*] posted on 30-8-2019 at 15:31
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]

1B536946-C7CC-4249-839F-0919C0802D2D.png - 5kBA325C02D-711B-4232-8F32-C8D1D87350C6.png - 5kB
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Boffis
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[*] posted on 31-8-2019 at 03:47


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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[*] posted on 31-8-2019 at 04:04


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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[*] posted on 31-8-2019 at 04:28


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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[*] posted on 1-9-2019 at 04:23


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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[*] posted on 1-9-2019 at 08:01


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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