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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 16
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Original Articles

A Convenient Procedure for the Synthesis of N-Substituted-N-glycolyl-1,2-aminoethanol Derivatives

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Pages 2235-2240 | Received 05 Mar 1993, Published online: 23 Sep 2006

References

  • Alcaide , B. , de la , R. F. , Pradilla , C. , López-Mardomingo , R. , Pérez Ossorio and Plumet , J. 1981 . J. Org. Chem. , 46 : 3243 See, for instance)
  • Alcaide , B. , Escobar , G. , Gonz , J. L. , Ález-Simó , C. , López-Mardomingo , R. , Pérez Ossorio and Plumet , J. 1982 . Tetrahedron etters , 23 : 2033
  • Alcaide , B. C. , López-Mardomingo , R. , Pérez Ossorio , Plumet , J. , Phan-Tan-Luu , R. and Sargent , M. 1985 . Can. J. Chem. , 63 : 2241
  • Alcaide , B. , Dominguez , G. C. , López-Mardomingo , R. , Pérez Ossorio and Plumet , J. 1986 . J. Chem. Soc. Perkin , 2 : 99
  • Alcaide , B. , García Gravalos , M. D. , López , B. , Plumet , J. and del Valle , A. 1992 . Heterocycles , 33 : 55
  • Murahashi , S. , Mitzue , Y. and Ike , K. 1987 . J. Chem. Soc. Chem. Comm. , : 125 Close derivatives such as oxamates (R2N-CO-CO2R) could be obtained by double carbonylation of amines and alcohols. The method appears not be applied to aminoalcohols like 2. See For a convenient revision on carbonylation reactions, see
  • Max Roundhill , D. 1992 . Chem. Rev. , 92 : 1
  • Inoue , S. and Matsumura , G. 1979 . Carbohydr. Res. , 74 : 361 N-glycolylneuraminyl derivatives were identified in a trout-egg glycoprotein. See
  • Alcaide , B. C. , López-Mardomingo , B. , López , R. , Pérez Ossorio and Plumet , J. 1985 . J. Heterocyclic Chem. , 22 : 289
  • Sodium borohydride reduces cyclic anhydrides to lactones and cyclic imides to ω-carbinol lactams. See:
  • Bailey , D. M. and Johnson , R. E. 1970 . J. Org. Chem. , 35 : 3574 Cyclic anhydrides:
  • Wijnberg , J. B.P.A. , Shoemaker , H. E. and Speckamp , W. N. 1978 . Tetrahedron , 34 : 179 Cyclic imides:
  • Chamberlin , A. R. and Chung , J. Y.L. 1983 . J. Am. Chem. Soc. , 105 : 53
  • Hart , D. J. and Yang , T. K. 1983 . J. Chem. Soc. Chem. Comm. , : 135
  • Bernardi , A. , Micheli , F. , Potensa , D. , Scolastico , A. and Villa , R. 1990 . Tetrahedron Letters , 31 : 4949
  • The reaction of the morpholine derivatives (3) with LiAlH4/THF at 0°C gives the N-glycolyl derivatives (1) with moderate yield and recycling of the starting aminoalcohol (2)

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