ORGLIST: Deprotection of a trityl group

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From: Ken Knott (esprcorn$##$
Date: Wed Dec 15 2004 - 23:38:50 EST

I have having issues deprotecting a trityl group from an amine. According
the the publsihed papers the deprotection should occur easily with an acidic
media. I have tried HCl, HBr, triflouroacetic acid, and others. Suffice to
say the deprotection does not occur.

I have also tried sodium in methanol based on a paper. This made a mess and
did not work.

Lastly I have tried a dehydrogenation with Pd/C catalyst 10%. This appears
to have worked though after a day at atomospheric pressure it appears to
have only been about 10-20% effective. I work in an inorganic lab and
dehydrogenation appartus is not readily available for increased pressures.
I used a baloon.

Can someone suggest possible other routes, an improved method for the
dehydrogenation, or possibly suggest a better catalyst?

Oh, and if someone can tell me why the deprotection isn't working with
acids, I am curious as everything I've seen indicaies that it should be very



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