Summary of Improvements in the Synthesis Procedure

 

 

Lloyd Garrick.

 

 

 

Williamson Ether Synthesis:

 

 

 

 

 

 

Reductive Amination:

 

 

 

 

 

Carbamoylation:

 

 

 

 

 

 

 

 

 

Peroxidation:

 

 

 

I have been using a slightly different workup method, which may be more efficient and will lessen the chance of any peroxide in the final product.

 

For the production run, the reaction solution (mostly methanol) was quenched with aqueous carbonate, most of the product oiled out. The decant was then stripped of most methanol and extracted for additional product.

 

What I did was to strip the methanol 1st (20-30*C MAX), decant from the oiled out product, then add the carbonate solution to quench residual peroxide, then extract the decant with EtOAc to recover all product. No aqueous phases contained any product. The combined EtOAc solutions then washed twice with brine, and stripped to residue. All residual peroxide (there really shouldn’t be any at this point, and a simple check with starch-iodine paper confirms) will remain in the aqueous, not the EtOAc.