ORGLIST: Deprotection of the indole N

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From: Peng Gao (pgao00$##$st.lzu.edu.cn)
Date: Fri May 12 2006 - 06:49:10 EDT

Dear Colleagues£¬

  Recently I was confused by the deprotection of the indole N. The protection
group of the indole N is Bn, because of the ¦Á¦Âunsaturated carbonyl and another
ester group in my molecular, it can¡¯t be deprotected by Na / NH3(l) and Pd / H2.
I tried other methods from crossfire and scifinder (all kinds of lewis
acid,;t-BuOK, DMSO; protonic acid; LDA), they all didn¡¯t work or made the
substrate decompose. At this time, my boss suggest me change the Bn to PMB, but
when I make it to PMB, I tried all the lewis acid, protonic acid , DDQ, CAN.
Unfortunately, the reaction is also just like the Bn compound. Did someone know
the other methods of deprotection of the Bn or PMB group at the indole N.

  Any suggestion will be welcome. Thank you for your attention and help!

-Peng

Peng Gao
Prof. Xu Group
National Laboratory of Applied Organic Chemistry
(http://sklaoc.lzu.edu.cn/)
Department of Chemistry, Lanzhou University
Lanzhou P.R. China
Email: pgao00$##$st.lzu.edu.cn
       

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