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Topic: Can this reduction be made???  (Read 4370 times)

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Offline lutesium

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Can this reduction be made???
« on: July 25, 2009, 04:25:53 PM »
Dear Sir/Ma'am

Is this reaction scheme true?

Offline nj_bartel

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Re: Can this reduction be made???
« Reply #1 on: July 25, 2009, 07:30:02 PM »
Seems like you'd just deprotonate the pyridinium then be stuck with a standard alkoxide.

Offline kiwi

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Re: Can this reduction be made???
« Reply #2 on: July 26, 2009, 08:21:49 PM »
Nope, neither step will work. There are many simple approaches to these sorts of compounds, due to their psychoactive (and illegal) nature.

Offline gfunk

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Re: Can this reduction be made???
« Reply #3 on: July 26, 2009, 11:13:47 PM »
I'd rather dehydrate and then hydrogenate.  Funny, that product is one methyl group away from methamphetamine...
Grad Student - Organic Chemistry
University of Alberta

Offline lutesium

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Re: Can this reduction be made???
« Reply #4 on: July 28, 2009, 03:47:01 PM »
No this product is the de-hydroxylased form of Adrenaline! I would write Adrenaline but the two Hydroxyl Groups interact with the Pyridine!

We're just working on the reduction of the Benzylic -OH deoxygenation which is probably (correct me if I'm wrong) the hardest deoxygenation!
 
                                               Ph-(CH-OH)-R



Lutesium...

Offline g-bones

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Re: Can this reduction be made???
« Reply #5 on: August 04, 2009, 07:51:35 PM »
I would say that pyridine would not be a strong enough base to create an alkoxide, if so the equilibrium would be so small favoring the alkoxide it would be almost negligable, I agree with the guy above me that would dehydrate and then hydrogenate. 

On a second thought the dehydration would yield a vinyl amine, which would more than likely tautomerize to the imine, which could then be reduced.

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