I have synthesized the molecule below possessing a doubly, boc protected heterocyclic amine and a terminal alkyne.
Upon attempting a TFA/$\ce{CH2Cl2}$ Boc deprotection I believe my alkyne is being hydrolysed.
1.) I wish to use TMSI to perform the boc deprotection but cannot find information on how it acts in the presence of alkynes. Would TMSI iodinate, silylate or otherwise interact with the alkyne?
2.) Is there any way to make use of TFA/$\ce{CH2Cl2}$ and prevent the alkyne hydrolysis?