ORGLIST: MONO PROTECTION OF DIAMINES

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From: Christopher Whicker (c.whicker$##$uws.edu.au)
Date: Mon Apr 19 1999 - 22:29:44 EDT



Dear list members,
I am currently looking for a method to mono protect ethane-1,2-diamine
(ethalenediamine). I wish to use the protected diamine in a double
condensation reaction with a phenol, thus producing a six membered ring
incorporating the 1,2 positions of the benzene ring.
C1-O-CH2-N(CH2CH2NHP)CH2-C2.
I believe the ether link will be susceptible to acidic
deprotection,resulting in the reformation of the phenol.
I an also considering the same reaction method with a hydroxyamine
(ethanolamine etc) as such a protecting group that is also selective for
primary alcohols over amines would be ideal.

I have in mind Fmoc, as it can be removed under mild conditions, but I
would be grateful for any input from somebody with experimental experience
in this area.

Kindly yours

CW


Christopher Whicker
Chemistry Deparment
University Western Sydney, Macarthur
P.O Box 555 Campbelltown
NSW 2560
Ph. (02) 46203797
Fax.(02) 46203025


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