ORGLIST: Hydrazin-imine reduction.

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From: Jonas Nilsson (jonni$##$ifm.liu.se)
Date: Mon Jan 08 2001 - 04:21:15 EST

Hello.

I have a compund containing an aldehyde and two methylesters, which I'm
doing reductive amination on.

This works fine with ordinary amines (even very steric hindred ones) using
Mol. Sieves / MeOH/amine and then NaBH4 or pyridine-BH3 (r.t.).
However when the amine is a BOC-protected hydrazine (t-Butylcarbazate,
BOC-NH-NH2) the reductive reagent doesn't seem to bee strong enough. Do you
have any suggestions for this transformation?

R-O-CH2-CHO + NH2-NHBOC -> R-O-CH2-CH2-NH-NHBOC
R containing methyl esters

Regards
/jN

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