idk
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Eschweiler-Clarke reaction with protected amines
Does the reaction proceeds with N-acyl protected amines, or the hydrolysis is inevitable? If acyl-protecting is not sufficient then are there any
protecting groups that coud make it?
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Sigmatropic
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The Eschweiler-Clarke proceeds through an iminium ion. N-acyl compounds can't form an iminium ion. Benzyl protection comes to mind. Are you trying to
protect one amine while reacting the other or getting mono methylation on one amine?
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Loptr
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You could make the tosylate and then alkylate with an alkyl halide. I have a reference I will dig up for you shortly.
Couldn't you just alkylate with an alkyl halide? The nitrogen of the amide is less nucleophilic due to the resonance stabilization of the nitrogen
lone pair provided by the amide carbonyl group. This means there is less chance of over alkylation. It might require more forcing conditions.
[Edited on 7-9-2018 by Loptr]
"Question everything generally thought to be obvious." - Dieter Rams
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CuReUS
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It does,but you need a stronger reducing agent then
HCOOH-https://www.tandfonline.com/doi/abs/10.1080/0039791770940927... | Quote: | | If acyl-protecting is not sufficient then are there any protecting groups that coud make it? |
You might not
even need a PG,if you tell what you are aiming for  means ? https://pubs.acs.org/doi/abs/10.1021/ja01125a053
btw,this looks interesting -https://pubs.acs.org/doi/10.1021/ol401362k
[Edited on 7-9-2018 by CuReUS]
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