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Topic: Ways of making alpha-amino ketones?  (Read 5457 times)

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Offline janapix

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Ways of making alpha-amino ketones?
« on: April 06, 2012, 03:31:27 PM »
I've been trying to come up with different ways of synthesizing alpha-amino ketones and thus far have:
(i) NH3 reacting with an alpha-bromo ketone, where nucleophilic substitution enabled replacement of Br by NH2. HBr by-product.

Is this feasible?
Are there other ways of making alpha amino-ketones? This is for an undergraduate laboratory assignment so the simpler the technique, the better.

If you could just tell me the reagents, reaction type (maybe reaction conditions as a bonus) I woul dbe very grateful.

Offline discodermolide

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Re: Ways of making alpha-amino ketones?
« Reply #1 on: April 06, 2012, 03:36:56 PM »
I've been trying to come up with different ways of synthesizing alpha-amino ketones and thus far have:
(i) NH3 reacting with an alpha-bromo ketone, where nucleophilic substitution enabled replacement of Br by NH2. HBr by-product.

Is this feasible?
Are there other ways of making alpha amino-ketones? This is for an undergraduate laboratory assignment so the simpler the technique, the better.

If you could just tell me the reagents, reaction type (maybe reaction conditions as a bonus) I woul dbe very grateful.


Have a look at the following.
http://www.mendeley.com/research/synthesis-alpha-amino-ketones-via-selective-reduction-acyl-cyanides/
and

Org Lett. 2001 May 17;3(10):1519-21.
A simple preparation of ketones. N-protected alpha-amino ketones from alpha-amino acids.
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Offline Honclbrif

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Re: Ways of making alpha-amino ketones?
« Reply #2 on: April 06, 2012, 05:45:22 PM »
Protecting either the amine or the ketone is going to be essential, otherwise you will form an immine.
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Offline Alberto_Kravina

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Re: Ways of making alpha-amino ketones?
« Reply #3 on: April 07, 2012, 12:17:14 PM »
Neber Rearrangement could be a good route

Offline discodermolide

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Re: Ways of making alpha-amino ketones?
« Reply #4 on: April 07, 2012, 12:29:20 PM »
Neber Rearrangement could be a good route


Nice. I was not aware of this reaction:))
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