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Topic: O-methyl oxime reduction.  (Read 1737 times)

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Offline OrganicDan96

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O-methyl oxime reduction.
« on: May 25, 2018, 07:14:01 PM »
I have a synthesis that involves converting a ketone to an O-methyloxime then reduction with BH3.THF to give an amine. is there a reason for the methyl group? Because O-methylhydoxylamine hydrochloride is rather expensive and i would like to see if i can try the synthesis with the OH Oxime to save cost but could this be a problem?

Offline pgk

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Re: O-methyl oxime reduction.
« Reply #1 on: May 29, 2018, 10:55:54 AM »
Yes, there is. You need an excess of diborane and have to heat above 100oC, to finally obtain lower yields:
Reduction of oximes, oxime ethers, and oxime esters with diborane. Novel synthesis of amines, J. Org. Chem., (1969), 34(6), 1817–1821
https://pubs.acs.org/doi/abs/10.1021/jo01258a062?src=recsys&journalCode=joceah
« Last Edit: May 29, 2018, 11:22:18 AM by pgk »

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