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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: zuriel on March 10, 2014, 01:48:25 PM

Title: Cleaving a pivalate ester
Post by: zuriel 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  :)
Title: Re: Cleaving a pivalate ester
Post by: Dan 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.
Title: Re: Cleaving a pivalate ester
Post by: zuriel on March 11, 2014, 07:35:05 AM
Thanks for the tip, Dan! Would you have a general procedure at hand for the aminolysis?
Title: Re: Cleaving a pivalate ester
Post by: zuriel on March 11, 2014, 08:18:14 AM
Also would aminolysis not make an amide where the pivalate is?
Title: Re: Cleaving a pivalate ester
Post by: TheUnassuming 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. 
Title: Re: Cleaving a pivalate ester
Post by: SDVENHI 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