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Topic: Cleaving a pivalate ester  (Read 2759 times)

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Offline zuriel

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Cleaving a pivalate ester
« on: March 10, 2014, 01:48:25 PM »
Hi folks,

Can anyone suggest other possible reagents for cleaving this pivalate ester? Sodium hydroxide and HCl were tried but to no avail....starting material recovered. Looking for something that won't affect the other functionalities if at all possible - thanks  :)

Offline Dan

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Re: Cleaving a pivalate ester
« Reply #1 on: March 11, 2014, 05:26:10 AM »
I'd give aminolysis with ammonia a shot. There's a lot of bulk here, I can see this being tough.
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Offline zuriel

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Re: Cleaving a pivalate ester
« Reply #2 on: March 11, 2014, 07:35:05 AM »
Thanks for the tip, Dan! Would you have a general procedure at hand for the aminolysis?

Offline zuriel

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Re: Cleaving a pivalate ester
« Reply #3 on: March 11, 2014, 08:18:14 AM »
Also would aminolysis not make an amide where the pivalate is?

Offline TheUnassuming

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Re: Cleaving a pivalate ester
« Reply #4 on: March 11, 2014, 10:30:35 AM »
Pig liver esterase.
It works great for cleaving esters when I'm estimating pk/pd of a pro-drug.  One of which was actually a piv group. 
When in doubt, avoid the Stille coupling.

Offline SDVENHI

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Re: Cleaving a pivalate ester
« Reply #5 on: April 19, 2014, 02:43:29 AM »
This looks like a tough hydrolysis.  As suggested above, aminolysis could do the job.  I would also consider hydrazine hydrate in an alcohol such as ethanol

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