AW: ORGLIST: amine protection

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From: Bohlen, Jost T. (bohlen$##$fiz-chemie.de)
Date: Wed Sep 27 2000 - 10:18:21 EDT

The ChemInform Reaction Library suggests among others LiAlH4 in THF or Et2O.
The reaction usually proceeds below room temperature.

Jost T. Bohlen
FIZ CHEMIE BERLIN

> -----Ursprüngliche Nachricht-----
> Von: César Barbero [SMTP:cbarbero$##$exa.unrc.edu.ar]
> Gesendet am: Mittwoch, 27. September 2000 15:22
> An: Multiple recipients of list orglist
> Betreff: ORGLIST: amine protection
>
> Dear people,
> I'm trying to protect a secondary amino(diphenylamine) group in a
> molecule using the formation of an amide. The protection step (reaction
> with 10% acetic anhidride in acetic acid and a drop of concentrated
> sulfuric acid) works very well but after the intended reaction we are
> unable to hydrolize the amide. We hace tried with 10 % KOH in water and
> ethanol, 10% sulfuric and HCl, CO3K2 in CH3OH, t-ButO- in tButOH
> without sucess. Any suggestions? (other than to change the protecting
> group).
> Thank you in advance
>
> Dr. Cesar Barbero
>
>
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>
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