From: will jones (willjones46$##$hotmail.com)
Date: Wed May 17 2006 - 10:48:10 EDT
I would have thought that the ester would get hydrolysed by the KOH...
>From: "Guido de Silvestri" <guidods$##$etb.net.co>
>To: <everybody$##$orglist.net>
>Subject: RE: ORGLIST: Deprotection of the indole N
>Date: Tue, 16 May 2006 15:46:00 -0500
>
>
>Dear Mr. Gao...
>
>It may be waited that the Indole could have the secondary amines and the
>aromatic substances properties, but it does not have the typical amine
>properties.
>
>The p electrons from the nitrogen incorporated to the pi orbital, leave
>nitrogen without no shared electrons, causing to the substance, the
>presence of a very weak basic property, even though the indole can be
>rated as a secondary amine. I think that the hydrogen atom from the
>nitrogen should be than acid enough, which can be subtract with
>potassium hydroxide.
>
>So... maybe that is what happening... Try first with KOH, heating the
>system to reflux.
>
>Best regards,
>
>Guido de Silvestri
>
>
>
>
>
>-----Mensaje original-----
>De: everybody-bounces$##$orglist.net [mailto:everybody-bounces$##$orglist.net]
>En nombre de Peng Gao
>Enviado el: Viernes, 12 de Mayo de 2006 05:49 a.m.
>Para: everybody$##$orglist.net
>Asunto: ORGLIST: Deprotection of the indole N
>
>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
>
>
>_______________________________________________
>ORGLIST - Organic Chemistry Mailing List
>Website / Archive / FAQ: http://www.orglist.net
>To post a message (TO EVERYBODY) send to everybody$##$orglist.net
>To unsubscribe, send to everybody-request$##$orglist.net the message:
>unsubscribe your_orglist_password your_address
>
>
>_______________________________________________
>ORGLIST - Organic Chemistry Mailing List
>Website / Archive / FAQ: http://www.orglist.net
>To post a message (TO EVERYBODY) send to everybody$##$orglist.net
>To unsubscribe, send to everybody-request$##$orglist.net the message:
>unsubscribe your_orglist_password your_address
_______________________________________________
ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net
To post a message (TO EVERYBODY) send to everybody$##$orglist.net
To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address
This archive was generated by hypermail 2.1.4 : Tue Feb 13 2007 - 14:17:01 EST