[collin_det]

Hello.

I have just tried to protect my amine today. I did it on 40 mmol scale in DCM (60 ml.) It is a primary amine. I activated it with 1 eq. triethyl amine and added 1.1 eq. BOC anhydride in one portion at RT.

I am afraid that it now will Di protect it instead, as I did not cool it under addition? Any of you who has tried it under these conditions?

Every response will be apreciated.

Thanks.

[OC pro]

You will get only mono-Boc. Di-Boc can be made by using DMAP stoichiometric. But with 1.1equiv. Boc2O or even excess and triethylamine you will get >95% only mono-Boc.

[collin_det]

Thank you very much for your answer.

I havent tried it with alkyl amines before, so I was afraid that they were too active.

But regarding the Di BOC protection. I have actually done it with an aromatic amine, with a little over 2 eq. BOC anhydride, and DMAP (catalytic only) in chloroform. It took about some hours at RT and then it was diprotected. But I have to tell that it did not work on all my substrates.

But thanks again for you answer.

It made me sleep at night