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Microwave-Assisted Protection of Primary Amines as 2,5-Dimethylpyrroles and Their Orthogonal Deprotection
Primary amines can be readily doubly
protected as <i>N</i>-substituted 2,5-dimethylpyrroles.
Although this protecting group
is stable toward strong bases and nucleophiles, long reaction times
are required for both the protection and deprotection steps, generally
resulting in low deprotection yields. By employing microwave irradiation,
protection and deprotection reaction times are dramatically reduced.
Furthermore, deprotection with dilute hydrochloric acid in ethanol
increases reaction yields. Diverse deprotection conditions have been
developed in conjunction with microwave irradiation, so that protection
as an <i>N</i>-substituted 2,5-dimethylpyrrole can be orthogonal
to other standard amine protecting groups, such as <i>tert</i>-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl
(Fmoc)