TY - JOUR
T1 - Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection
AU - Walia, Amit
AU - Kang, Soosung
AU - Silverman, Richard B.
PY - 2013/11/1
Y1 - 2013/11/1
N2 - Primary amines can be readily doubly protected as N-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 N-substituted 2,5-dimethylpyrrole can be orthogonal to other standard amine protecting groups, such as tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl (Fmoc).
AB - Primary amines can be readily doubly protected as N-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 N-substituted 2,5-dimethylpyrrole can be orthogonal to other standard amine protecting groups, such as tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl (Fmoc).
UR - http://www.scopus.com/inward/record.url?scp=84887102896&partnerID=8YFLogxK
U2 - 10.1021/jo401778e
DO - 10.1021/jo401778e
M3 - Article
C2 - 24073706
AN - SCOPUS:84887102896
SN - 0022-3263
VL - 78
SP - 10931
EP - 10937
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -