From: Maringanti Krishna (maringanti9$##$yahoo.com)
Date: Fri Oct 29 2004 - 03:49:58 EDT
In a THF/CH2Cl2 solution of your amine, add sequentially CDI and alcohol, and leave it o/n.
If this fails, prepare a tBoc ester of your amine, take the Boc compound into THF, add potassium tert-butoxide, and then alcohol (add alcohol slowly, over 30 minutes)
If this fails, take a mixture of your amine, alcohol, and triethylamine (1 eq.) in CH2Cl2/Dioxane (25 mL per mmol) and add phosgene dissolved in toluene (you get 20% phosgene in toulene). Stirr for o/n. You will get a mixture of compounds, Urea + Carbamate. Inprinciple, you should be able to precipitate the urea in ether/ethyl acetate. Carbamates are soluble in ethylacetate.
If this also fails, try triphosgene/pyridine method.
You can try the reaction in the sequence given.
Dr. Krishna Maringanti
Medicinal Chemistry Division
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