Any suggestions of synthetic routes which could lead to mono N-methylation of an unsaturated aliphatic primary amine, exclusively?

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Taniya Adak

Yes, I'm considering N-formylation and then reduction in the following step. Will update how it goes. Thanks!

Sanjiv Tomer

React the substrate with any of the chloroformate, ie. methyl chloroformate or ethyl chloroformate. Further reduce the obtained carbamte with LAH to give the desired product.

Marcelo Preite

I would give a try to an Eischweiler-Clarke methylation.

Update: I carried out N-formylation of primary amine using ethyl formate and reduced the resulting formamide with LiAlH4 to yield mono-methylated amine, solely. 80% overall yield. Thanks, all of you.

Dear Taniya,

Thanks for the update.