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Author Topic: N-detosylation of heterocycle  (Read 3905 times)

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asa029

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N-detosylation of heterocycle
« on: May 28, 2011, 10:55:40 PM »

I need to N-detosylate a heterocyclic compound. I've seen different procedures in the litterature, but the yield is usually pretty low and the reaction conditions are pretty harsh. Such procedures include using lithium or sodium metal in methanol, different kinds of amalgams or very strong basic conditions. I've also seen an article describing using a two-phasic system and a PTC. Does anyone have any experience or thoughts on the subject?
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rucik5

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Re: N-detosylation of heterocycle
« Reply #1 on: May 29, 2011, 12:18:39 AM »

There was a paper (in Org Lett I think) released quite recently about a detosylation procedure with samarium iodide, base (triethylamine or pyrrolidone) and water. They managed to remove the tosyl from an Ts-N-Boc cmpnd, leaving the Boc intact.



Here: http://pubs.acs.org/doi/abs/10.1021/ol802243d

They use 6 equivalents of it, but the whole reaction is complete in seconds, and 100ml 0.1M sln of SmI2 in THF is available from sigma. Yield are in 80-90% i believe.
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nox

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Re: N-detosylation of heterocycle
« Reply #2 on: May 29, 2011, 04:14:52 PM »

Is there anything Samarium iodide won't do?
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