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Synfacts 2009(5): 0580-0580
DOI: 10.1055/s-0029-1216550
DOI: 10.1055/s-0029-1216550
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Solid-Phase Synthesis of Amines via the Curtius Rearrangement
S. Sunami*, M. Ohkubo
Banyu Pharmaceutical Co., Ltd., Ibaraki, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)

Significance
Solid-phase synthesis of aryl, heteroaryl and sterically hindered alkyl amines using the Curtius rearrangement was described. Thus, Wang resin 1 reacted with carboxylic acids (3 mol equiv to OH residue of the resin), DPPA, and triethylamine in toluene to give the corresponding carbamate-anchored resins 2. Treatment of 2 with 50% TFA in dichloromethane afforded the amines 3 in 60 to >95% yield (19 examples).