[Reddart]

I am planning on protecting the alcohol on N,N-Diisopropylethanolamine with a THP group, but I am assuming I will need to protonate the amine first, and then THP? Perhaps TBDMS would be a better choice? I want to later be able to remove the group under acidic conditions (no F-).

[wildfyr]

Funny how this keeps coming up, but TBDMS will work like a champ. Use ~equimolar TBDMS-Cl with 2.1 eq imidazole as a catalyst/acid scavenger. Water workup, maybe run a little hexane column to separate out the siloxane dimer if some shows up. And it should hydrolyze in HCl afterwards, though something like TBAF is probably faster.

God I love TBDMS protection, easily my favorite reaction.

[kriggy]

You can protect by THP in DCM with catalytic amount of ptsa. Then just NaHCO3 wash and collumn if necessary