ORGLIST:reduction of O-methyl oximes to primary amines

Date view Thread view Subject view Author view Attachment view

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


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


+++ GMX - die erste Adresse für Mail, Message, More +++
Neu: Preissenkung für MMS und FreeMMS!

_______________________________________________ ORGLIST - Organic Chemistry Mailing List Website / Archive / FAQ: To post a message (TO EVERYBODY) send to everybody$##$ To unsubscribe, send to everybody-request$##$ the message: unsubscribe your_orglist_password your_address List coordinator: Joao Aires de Sousa (coordinator$##$

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Jan 16 2004 - 06:43:07 EST