A Nucleophilic Deprotection of Carbamate Mediated by 2-Mercaptoethanol
Thomas Scattolin, Tawfik Gharbaoui, Cheng‐yi Chen
Abstract
Carbamates, typically used for the protection of amines, including Cbz, Alloc, and methyl carbamate, can be readily deprotected by treatment with 2-mercaptoethanol in the presence of potassium phosphate tribasic in N,N-dimethylacetamide at 75 °C. This nucleophilic deprotection protocol is superior to the standard hydrogenolysis or Lewis acid-mediated deprotection conditions for substrates bearing a functionality sensitive to these more traditional methods.
Topics & Concepts
ChemistryHydrogenolysisCarbamateNucleophileDimethylacetamideLewis acids and basesPotassiumOrganic chemistryCombinatorial chemistryCatalysisSolventChemical Synthesis and AnalysisChemical Synthesis and ReactionsAsymmetric Hydrogenation and Catalysis