October 15, 2021, 04:56:54 PM
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Topic: Reducing an amide (to hemiaminal or amine) in the presence of an epoxide.  (Read 5349 times)

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Offline zeropoint

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Anyone know a reagent to accomplish this? Li based reagents probably won't work as the lewis acidic quality will weaken the epoxide C-O bonds. Any suggestions would be awesome!

Offline sjb

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Anyone know a reagent to accomplish this? Li based reagents probably won't work as the lewis acidic quality will weaken the epoxide C-O bonds. Any suggestions would be awesome!

Pure & Appl. Chem., Vol. 68, No. 4. pp. 843-848, 1996 - KEt3BH http://dx.doi.org/10.1351/pac199668040843

G Barbe and A B Charette, J Am Chem Soc, 2008, 130, 18 describes a Hanztch pyridine style reduction, perhaps (don't have access to the full paper, sorry) http://dx.doi.org/10.1021/ja077463q

Offline Dan

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DIBAL at low T ought to be highly chemoselective. There is certainly literature precedent for the efficient reduction of esters to aldehydes at -78oC in the presence of epoxides with DIBAL, so if you want to hit an amide it should be even easier.

eg. JACS, 2010, 132(8), 2542 - 2543
My research: Google Scholar and Researchgate

Offline Dan

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eg. JACS, 2010, 132(8), 2542 - 2543

Stupid emoticons, it's issue 8.

JACS, 2010, 132 (8 ), 2542 - 2543
My research: Google Scholar and Researchgate

Offline zeropoint

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G Barbe and A B Charette, J Am Chem Soc, 2008, 130, 18 describes a Hanztch pyridine style reduction, perhaps (don't have access to the full paper, sorry) http://dx.doi.org/10.1021/ja077463q

That's a great link. Unfortunately, I doubt that my amine is going to tautomerize, it's in an aromatic ring, making this reaction more difficult. Luckily, I have access to Charette and maybe can ask him more details about this. Thanks. Also, trying DIBAL-H

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