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Synfacts 2009(5): 0580-0580  
DOI: 10.1055/s-0029-1216550
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Synthesis of Amines via the Curtius Rearrangement

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
S. Sunami*, M. Ohkubo
Banyu Pharmaceutical Co., Ltd., Ibaraki, Japan
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Publikationsdatum:
22. April 2009 (online)

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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).