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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: JohnLocke on June 10, 2019, 02:17:20 PM

Title: Borane Amide Reduction
Post by: JohnLocke 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 (https://imgur.com/a/bLmnKns). 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!
Title: Re: Borane Amide Reduction
Post by: OrganicDan96 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
Title: Re: Borane Amide Reduction
Post by: hollytara on June 13, 2019, 08:59:36 PM
Will 1 equivalent of borane suffice?