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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 16
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Original Articles

Mono-Protected Diamines. N-tert-Butoxycarbonyl-α,ω-Alkanediamines from α,ω-Alkanediamines

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Pages 2559-2564 | Received 27 Jun 1990, Published online: 24 Oct 2006

References

  • Mattingly , P. G. 1990 . Synthesis , : 366 starting from the corresponding amino alcohols and isolated as hydrochlorides
  • Stahl , G. L. , Walter , R. and Smith , C. W. 1978 . J. Org. Chem. , 43 : 2285 N-(BOC)-1,6-diaminohexane-HCI prepared from 1,6-diaminohexane and S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in dioxane (58% yield). b) Hansen, J. B., Nielson, M. C., Ehrbar, U., Buchardt, O. Synthesis 1982, 404, use of BOCN3 with several α,ω-alkanediamines led to poor yields of the corresponding N-(BOC) analogues. c) Melchiorre, C., Quaglia, W., Picchio, M. T., Giardina, D., Brasili, L. Angeli, P. J. Med. Chem. 1989, 32, 79. d) Essen, H., Lai, J. Y., Hwang, K.J. J. Med. Chem. 1988, 31, 898, use of BOC-ON and 1,2-diaminoethane to prepare N-(BOC)-1,2-diaminoethane requiring a tedious chfomatographic separation from the BOC-OFF by-product. e) Nason, D. M., Jasys, V. J., Kelbaugh, P. R., Phillips, D., Saccomano, N. A., Volkmann, R.A, Tetrahedron Letters 1989, 30, 2337
  • Houssin , R. , Bernier , J.-L. and Henichart , J.-P. 1988 . Synthesis , : 259 starting from the corresponding aminoalkanoic acids

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