Mono-protected diamines. n-tert-butoxycarbonyl-α,ω- alkanediamines from α,ω-alkanediamines

Synthetic Communications

Volumn 20, Issue 16, 1990, Pages 2559-2564

  Krapcho, A Paul ^a   Kuell, Christopher S ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 53349112702     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397919008053205     Document Type: Article

References (3)

1. 1) Mattingly, P.G. Synthesis 1990, 366; starting from the corresponding amino alcohols and isolated as hydrochlorides.
2. 2) a) Stahl, C.G.L., Walter, R., Smith, C.W.J. Org. Chem. 1978, 43, 2285; N-(BOC)-1,6-diaminohexane.HCl 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 chromatographic separation from the BOC-OFF by-product. e) Nason, D.M., Jasys, V.J., Kelbaugh, P.R., Phillips, D., Saccomano, N.A, Volkmann, RA Tetrahedron Letters 1989, 30, 2337.
3. 3) Houssin, R., Bernier, J.-L., Henichart, J.-P. Synthesis 1988, 259; starting from the corresponding aminoalkanoic acids.