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Topic: How can this compound be synthesised???  (Read 18203 times)

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Offline lutesium

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How can this compound be synthesised???
« on: March 14, 2009, 01:37:48 PM »
From start to finish but how???
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Offline frenchy

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Re: How can this compound be synthesised???
« Reply #1 on: March 15, 2009, 05:40:04 PM »
well it depends where you'd like to start from. I'd probably go via a cyclisation myself.
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PhD student in synthetic Inorganic and Supramolecular chemistry.

Offline russellm72

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Re: How can this compound be synthesised???
« Reply #2 on: March 16, 2009, 10:57:28 AM »
What do you want it for lutesium or is it purely theoretical?

have you come up with any disconnections leading to for example cheap starting materials.

Have a look at alanine and amino ethanol...
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Offline alphahydroxy

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Re: How can this compound be synthesised???
« Reply #3 on: March 16, 2009, 01:26:27 PM »
How about this...?

Just thought of it in a couple of seconds - not sure if it's feasible...

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Offline sjb

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Re: How can this compound be synthesised???
« Reply #4 on: March 16, 2009, 03:07:58 PM »
Cis? Trans?

Another wacky idea, don't know how feasible it is mind.

I know you can form 3-chloropyridine from pyrrole and dichlorocarbene, so what about 4-methyloxazole treated in the same way then reduced? I appreciate there's not the aromatic stabilisation here?
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Offline russellm72

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Re: How can this compound be synthesised???
« Reply #5 on: March 17, 2009, 11:49:45 AM »
Quote from: alphahydroxy on March 16, 2009, 01:26:27 PM
How about this...?

Just thought of it in a couple of seconds - not sure if it's feasible...


I like your idea alphahydroxy but rather than Glycine just start from aminoethanol. Also where would you get the 1,2,-dichloroacetone from? A quick search in Aldrich shows the closest analogue as 1,1-dichloroacetyl chloride. I am also not so sure the imine would from in preference to a simple alkylation but it may be feasable. Also the compound would probably cyclise easily and all you'd need is a simple reduction. Mmmmm it all depends on the imine formation but a good short synthesis...
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Offline macman104

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Re: How can this compound be synthesised???
« Reply #6 on: March 17, 2009, 12:57:19 PM »
I would argue that it would be better to perform the cyclization the other way.  Using the two nucleophiles (OH and NH2) to attack primary halogens.  The only issue is the building up that strange looking chloro beta-amino alcohol.  I think this should work reasonable well.

I want to say hydroboration is the correct route, but I wonder if the chlorine is electronegative enough to stabilize the carbocation and cause the addition to go the other way and form the alpha-aminoalcohol...

I also put the dibromo, but really any dihalide should work.  Or start with ethene, and add whatever halide you want...
« Last Edit: March 17, 2009, 01:23:41 PM by macman104 »
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Offline sjb

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Re: How can this compound be synthesised???
« Reply #7 on: March 17, 2009, 01:05:31 PM »
Quote from: russellm72 on March 17, 2009, 11:49:45 AM
Also where would you get the 1,2,-dichloroacetone from? A quick search in Aldrich shows the closest analogue as 1,1-dichloroacetyl chloride. I am also not so sure the imine would from in preference to a simple alkylation but it may be feasable. Also the compound would probably cyclise easily and all you'd need is a simple reduction. Mmmmm it all depends on the imine formation but a good short synthesis...

Well, you could try 1,1-dichloroacetylchloride and dimethylcadmium or similar?

How facile do you think the cyclisation would be - I mean, I don't think DCM reacts readily with NaOH to form formaldehyde, does it? (or is that just because OH is a relatively poor nucleophile?)
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Offline macman104

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Re: How can this compound be synthesised???
« Reply #8 on: March 17, 2009, 01:22:43 PM »
Can you not just grignard 1,1-dichloroacetylchloride with methyl magnesiumbromide to get the 1,1-dichloroacetone?  Am I missing some obvious incompatibility?
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Offline aldoxime_amine

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Re: How can this compound be synthesised???
« Reply #9 on: March 17, 2009, 02:46:34 PM »
I think you are. The reaction won't stop at the ketone, atleast not completely. The tert alcohol, is preferred...
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Offline macman104

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Re: How can this compound be synthesised???
« Reply #10 on: March 17, 2009, 04:14:58 PM »
Hmmm...I'm not sure that would be a problem.  Aldehydes and even more so acid chlorides are far more reactive than their ketone counterparts.  You only encounter those tert-alcohol problems with esters because the resulting ketone is more reactive than the ester, so it reacts preferentially.
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Offline russellm72

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Re: How can this compound be synthesised???
« Reply #11 on: March 18, 2009, 05:55:18 AM »
Here we all are discussing this problem and the author of the original problem remains silent..

I think using 1,1-dichloroacetyl chloride and a soft metal approach would be Ok.

Macman the first step in your synthesis I have not encountered. I have not seen an amide behaving in such a standar Wittig type fashion can you elaborate please.....

R.




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Offline macman104

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Re: How can this compound be synthesised???
« Reply #12 on: March 18, 2009, 12:39:04 PM »
Russellm, I haven't either, and I don't actually have access to literature to verify whether it works.  Are amides compatible with wittig reactions?
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Offline russellm72

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Re: How can this compound be synthesised???
« Reply #13 on: March 19, 2009, 05:49:23 AM »
I would definetly say No then. Sorry I thought you had discovered a new reaction...
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Offline macman104

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Re: How can this compound be synthesised???
« Reply #14 on: March 19, 2009, 06:11:38 AM »
Quote from: russellm72 on March 19, 2009, 05:49:23 AM
I would definetly say No then. Sorry I thought you had discovered a new reaction...
Haha, nah.  I'm perfectly happy to be wrong, and still a student myself.  But using the knowledge I've gained, I don't see much wrong with "wittig-ing" an amide.  Is there something about the wittig reaction and amide that would create an incompatibility?  Is the amide just acidic enough to destroy the ylide?

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