[dec1624]

I have to N-allylate a molecule containing an amino alcohol functionality or basically get the allyl part on the nitrogen one way or another.

Allylation with K2CO3 and allyl bromide (60 deg) worked but caused one of my TBS groups to fall off. Stirring at room temp doesn't result in any reaction though. Is there anything else I can try?

An alternative method was to try reductive amination using acrolein and I've tried this with NaCNBH3 and NaBH(OAc)3. Both times I end up with starting material. Scifinder only has 2 references on reductive aminations with acrolein on amino alcohols - both of which are in russian >_<

My supervisor wants me to boc protect the free primary amine in the amino alcohol and then do allylation with a strong base (presumably NaH and allyl bromide?) but that doesn't quite make sense to me since those conditions would probably result in O-allylation and cleavage of the TBS?

So what do I try now? Some help will be greatly appreciated.

[xiaoruan]

I have to N-allylate a molecule containing an amino alcohol functionality or basically get the allyl part on the nitrogen one way or another.

Allylation with K2CO3 and allyl bromide (60 deg) worked but caused one of my TBS groups to fall off. Stirring at room temp doesn't result in any reaction though. Is there anything else I can try?

An alternative method was to try reductive amination using acrolein and I've tried this with NaCNBH3 and NaBH(OAc)3. Both times I end up with starting material. Scifinder only has 2 references on reductive aminations with acrolein on amino alcohols - both of which are in russian >_<

My supervisor wants me to boc protect the free primary amine in the amino alcohol and then do allylation with a strong base (presumably NaH and allyl bromide?) but that doesn't quite make sense to me since those conditions would probably result in O-allylation and cleavage of the TBS?

So what do I try now? Some help will be greatly appreciated.

Recently I also have to N-allylate a molecule, a second amine and a a-brominated acetophenone, i don't know what the structure your molecule, just try to stir at room temp add in slight KI.