Re: ORGLIST: (no subject)

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From: Sachin Chaphekar (purvi_chaphekar$##$yahoo.com)
Date: Wed Aug 02 2006 - 23:42:51 EDT


Hi! Will,
 
Are you sure that your amine does not form a salt with your glyoxalic acid?
Besides the glyoxalic acid, since contain an aldehydic fucntion also may condense with amine to get a schiff base.
Take such things into consideration and then decide the best system/approach.
 
Good Luck
 
Sachin


----- Original Message ----
From: will jones <willjones46$##$hotmail.com>
To: everybody$##$orglist.net
Sent: Monday, July 31, 2006 10:49:27 PM
Subject: ORGLIST: (no subject)


Hi guys,

I've been using triacetoxyborohydride to effect a variety of reductive
alkylation reactions; however, I am having a couple of problems involving
the reductive alkylation of an aliphatic primary amine in the presence of
glyoxylic acid.

The glyoxylic acid is in the hydrate form, and I think that the
triacetoxyborohydride is decomposing before carrying out any reduction.

So, do you think that if I carry out the reaction in the presence of
molecular sieves, preforming the imine and removing any hydrate associated
with the glyoxylic acid then I might have more success?

My alternative is to use CNBH3, but I've already set-up all my other
reactions with (OAc)3BH and have found them to go really smoothly...

Awaiting your comments...

Cheers

Will


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