ORGLIST:reduction of O-methyl oximes to primary amines

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From: samarium Steiner (neptunium$##$gmx.net)
Date: Tue Jan 06 2004 - 03:43:16 EST


hello!

I'm looking for a valuable method to reduce O-methyl oximes to a primary
amine. In the molecule used, there's also a BOC protecting group present, which
shouldn't be affected by the rxn (thus, LAH, AlH3, or NaBH4 with Ni or Co
salts doesn't work).
I have tried BH3-THF which works, but the yield is not satisfactory (some
30-50% after isolation). I'm not sure if the problem lies also in the somewhat
difficult workup when using BH3 (I guess there are some borane-amine coplexes
which, in another rxn, we first had to destroy them acidically. but due to
the presence of a BOC group, this strong acidic conditions do not work here).

Is anyone experienced with that type of conversion? Any alternative idea?

Thank you, greetings

samarium

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