ORGLIST: Imine Reduction with NaBH4

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From: kmorendha (mailbox$##$prolificint.com)
Date: Tue Feb 21 2006 - 09:41:39 EST

This is in continuation to my earlier posting for C=O to CH2 reduction :

What do you think, if I reduce the Imine formed by reaction between these two reactants with NaBH4 ?

Imine formation :
----------------------
                                              
Ph-CO-CH=CH-COOC2H5

+

CH(CH3)-H2N COOC7H7

to

Ph-CO-CH2-CH(COOC2H5)-NH-CH(CH3)-COOC7H7
                                            
                                            

Now reducing the Imine formed above with NaBH4 in Methanol to get the final product :

Ph-CH2-CH2-CH(COOC2H5)-NH-CH(CH3)-COOH

i.e. : getting C=O to CH2 & C7H7 to COOH.

May it work ? If yes, then can I get some experimental & work-up suggetions for this ?

Awaiting your suggetions !

Thanks in advance,
Kamal


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