Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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The Synthesis of $\alpha$-lhnctionalized Benzykmine

$\alpha$-Functionalized Benzylamine의 합성

  • Kim, Hyeung-Jae (Department of Chemistry,Changwon National University) ;
  • Cho, Su-Dong (Department of Chemistry,Changwon National University) ;
  • Ahn, Chul Jin (Department of Chemistry,Changwon National University) ;
  • Joo, Woo-Hong (Department of Biology, Changwon National University) ;
  • Shin, Dong Soo (Department of Chemistry,Changwon National University)
  • Published : 20001000
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Abstract

$\alpha$-Functionalized benzylamine(Nu=OAc, OMe, N$_3$) will be very usefud as a starting material or synton in organic synthesis. We have investigated the first synthetic methodology of phthalimide-ben-zylacetate from benzylphthalimide, which are prepared in NBS/NaOAc/HOAc in chlorobenzene at 137$^{\circ}C$ for 12 hr in good yield. Finally, amino(phenyl)methyl acetate (1) was synthesized from phthalimide-benzyl acetate under NH$_2$NH$_2$/HOAC.

$\alpha$-Functionalized benzylamine(Nu=OAc, OMe, $N_3$)은 유기합성의 출발물질 또는 synthon으로서 매우 유용할 것이다. 본 연구에서는 benzylphthalimide를 137$^{\circ}C$, chlorobenzene 용매 하에서 NBS/NaOAc/HOAc조건을 사용하여, 높은 수율로 phthalimide-benzyl acetate을 얻는 방법을 개발하였다. 마지막으로, phthalimide-benzyl acetate을 $NH_2NH_2$/HOAc 조건 하에서, amino(phenyl)methyl acetate (1)을 합성하였다.

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References

  1. J. Med. Chem v.38 Lebreton, L.;Curet, O.;Gucddari, S.;MarmrGF.;Bernard,S.; Burstein, C.; Milcent, R.
  2. Synthetic Comm. v.25 no.8 Mitchell, D.;Koenig, T.
  3. J. Am. Chem. Soc. v.104 Bergeron, R.J.
  4. Synlett Nor, M.
  5. Angew. Chem. Int. Ed. Engl. v.33 Effenberger, F.
  6. Angew. Chem. Int. Ed. Engl. v.35 Bole, C.;Bienewald, F.;Seger, A.
  7. J. Org. Chem v.32 Tuleen, D.L.;Marcum, V.C.
  8. J. Org. Chem. v.44 Worley,J. W.
  9. J. Tetrahdron Lett v.28 Hashirnoto, H.; Kawa M.; Saito, Y: Date, T: Horito,S.; Yoshimura
  10. Tetrahedron Lett. v.39 Baker, S. R.;Parsons, A. F.;Wilson, M.
  11. Tetrahedron Lett v.39 Barberis, C.;Voyer, N.
  12. Hetrocyclic Chem. v.33 Kim, S. K.;Cho, S. D.;Moon, J. K.;Yoon, Y. J.
  13. Tetrahedron Lett v.40 Shin, D.S.;Kim, H. J.;Ahn, C.;Cho, S. D.;Falck, J. R.