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Topic: Borane Amide Reduction  (Read 1388 times)

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Offline JohnLocke

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Borane Amide Reduction
« on: June 10, 2019, 02:17:20 PM »
I'm trying to figure out the mechanism for reduction of an amide to an amine using borane (or BH3-THF) followed by HCl. My proposed mechanism is here. I am assuming in the final step there is a proton migration from the nitrogen to the unsaturated carbon? I am curious if there is a better way to explain the reaction.

Thanks!
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Offline OrganicDan96

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Re: Borane Amide Reduction
« Reply #1 on: June 11, 2019, 04:42:47 PM »
almost i think you need an extra step, what is the oxidation state of the last compound in your mechanism
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Offline hollytara

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Re: Borane Amide Reduction
« Reply #2 on: June 13, 2019, 08:59:36 PM »
Will 1 equivalent of borane suffice? 
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