ORGLIST:Hydrogenolytic N-benzyl removal

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From: samarium Steiner (neptunium$##$gmx.net)
Date: Mon Jun 16 2003 - 00:56:55 EDT

Hello,

my problem is: the removal of an N-benzyl protecting group doesn't work
under the following conditions. The compound in EtOH was tried to
hydrogenate
over Pd-C either acidic (2eq HCl) or basic (2eq NEt3) at 50deg C and several
pressures (3bar, 7bar) for 24h. Only small amounts of the desired product
were
formed. Usually this rxn occours even at r.t. and at atmospheric pressure H2
within 2-8h. Sometimes also Pd on BaSO4 is used as catalyst in the
literature,
but I didn't try this.

In my molecule are two other phenyl-moyeties (whereby one is as a
benzamide). Otherwise I would try to hydrogenate over Rhodium on activated
alumina.

Tnx for your help!

Regards,

samarium 

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