ORGLIST:Reductive Amination: suggestions

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From: Andrea Giordano (giordano$##$embl.de)
Date: Wed May 21 2003 - 11:13:06 EDT

Dear all,

I would like to ask you some suggestions regarding a reductive amination
procedure I would like to perform.
I have an aromatic ring with these substituents:
a -CHO group
a -OCH2COOMe group
a -OMe group
a -NO2 group

I need to trasform -CHO into -CH2-NH2 without affecting the NO2 and the
OCH2COOMe groups

a) a classical way, say NH3 + reductive agent, would trasform the ester into
the amide (right or wrong?) plus adding some by-products. Trasformation first
of the ester into the free acid i guess may overcome this (right or wrong?)
under the same conditions, but i would like to trasform -OCH2COOMe into -
OCH2COOH (which I need anyway...) at the very end.

b) Would hydrazine + reductive agent work well? Or something like allylamine or
NH2-CH2-Si(Me)3 or NH2-O-Si(Me)3 + reductive agent?? Or, why not, something
LESS TOXIC??

So, my question is: do you know any procedure/reagents/conditions to achieve
the goal? Some updated references on reductive amination will also be well
accepted!
Thanks v.m.! 

-- 
Andrea Giordano
PhD student, Schultz group 
Gene Expression Program
EMBL
Meyerhofstrasse, 1 
69117 Heidelberg, Germany
tel: 0049 6221 387 498
fax: 0049 6221 387 206

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