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Topic: Primary amine to alcohol  (Read 4634 times)

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Offline tommy1

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Primary amine to alcohol
« on: March 21, 2012, 06:38:41 PM »
I am having trouble coming up with conditions to give me the best yield of the product I want.
I have cyclohexamine with two ester groups in the para position and CONH2 ortho and I want to convert the amine group to the hydroxyl.

Literature has been using bases at high temperatures, but i think this will just break my esters apart. Others use NaNO3 with weak acid, but they were aiming for a product where both esters were cleaved, and I want them to remain...
 I was thinking of a Schiemann type reaction, but not sure if the esters will be affected by the halogen.
Any suggestions for conditions or methods would be greatly appreciated! :)

Offline discodermolide

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Re: Primary amine to alcohol
« Reply #1 on: March 22, 2012, 08:36:23 AM »
I am having trouble coming up with conditions to give me the best yield of the product I want.
I have cyclohexamine with two ester groups in the para position and CONH2 ortho and I want to convert the amine group to the hydroxyl.

Literature has been using bases at high temperatures, but i think this will just break my esters apart. Others use NaNO3 with weak acid, but they were aiming for a product where both esters were cleaved, and I want them to remain...
 I was thinking of a Schiemann type reaction, but not sure if the esters will be affected by the halogen.
Any suggestions for conditions or methods would be greatly appreciated! :)

Have a look at Tet. Letts. 1995, 36(14), 2377. "A mild oxidation of aromatic amines". They use oxone.
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