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Topic: nitro reduction  (Read 3894 times)

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Offline wisconsinium

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nitro reduction
« on: September 18, 2012, 11:54:16 AM »
Good morning,
I am brainstorming some reactions and am unsure about some functional group compatibilities. As shown in the scheme, I want to reduce a nitro group in the presence of an alpha-keto ester. How stable is the alpha-keto ester in general? Anything I need to look out for in this transformation? I am worried that it might destroy the alpha-keto ester or somehow cyclize the product. Thanks
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Offline discodermolide

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Re: nitro reduction
« Reply #1 on: September 18, 2012, 12:04:41 PM »
I think you should isolate the amine as a salt, i.e. do the reduction under acidic conditions, then you will avoid problems with the ketone and the ester.
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Offline Schrödinger

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Re: nitro reduction
« Reply #2 on: September 18, 2012, 01:59:47 PM »
We probably cant use Sn/HCl due to the presence of other active reducible groups. But when there are 2 nitro groups, we usually use NaSH. Is that applicable here? Can it selectively reduce the nitro group?
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Offline OC pro

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Re: nitro reduction
« Reply #3 on: September 19, 2012, 10:10:51 AM »
Like disco said Pd/C as catalyst in H2-atmosphere under acidic conditions. But cyclization can be very fast in this case.
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Offline DrCMS

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Re: nitro reduction
« Reply #4 on: September 19, 2012, 10:50:03 AM »
What about Bechamp reduction?
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Offline OC pro

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Re: nitro reduction
« Reply #5 on: September 19, 2012, 01:28:45 PM »
Should also work (Fe + HCl). Zn and Sn instead of Fe and HOAc instead of HCl will also be fine. 
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