We have tried direct substitution using a variety of bases and leaving groups, as well as alkylation of the Boc-protected amine without success.
Hi Jeremy,
perhaps this is a bit naive, but can't you just use the 2-propynoyl chloride, make the amide with your primary amine and then reduce the carbonyl group with LiAlH4? A problem could be that the triple bond gets attacked as well (we had such problems with a double bond and an allyl amine). Not sure if the terminal H would survive this.
I see this is a fairly old question - have you solved it since?
Best,
Anne
Hi, Anne - thanks for the reply. Unfortunately, this problem never was resolved, and we have moved on to an entirely different strategy (not involving a propargylic amine). On the other hand, your suggestion is a good one. Perhaps we'll come back to it at some point. Thanks again!
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