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Novel Practical Deprotection of N-Boc Compounds Using Fluorinated Alcohols

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Abstract:

The thermolytic deprotection of N-Boc compounds was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvents. Even though the cleavage of the t-butylcarbamate (Boc) group can be achieved at solvent reflux temperature, the deprotection process was significantly accelerated under microwave-assisted conditions. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic N-Boc-amines.

Keywords: Boc-deprotection; hexafluoroisopropanol; microwave; trifluoroethanol

Document Type: Research Article

DOI: https://doi.org/10.1080/00397910802238718

Affiliations: Roche Palo Alto, Palo Alto, California, USA

Publication date: 2008-01-01

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