A convenient transformation of N-substituted ureas into N-(t-butoxycarbonyl)amines using a copper(II) salt-lithium t-butoxide system

Tetrahedron Letters

Volumn 40, Issue 47, 1999, Pages 8251-8254

  Yamaguchi, Jun ichi ^a   Shusa, Yuji ^a   Suyama, Takayuki ^a  

^a KANAGAWA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Azo; Azo compounds; Carbamates; Copper; Copper compounds; Ureas

Indexed keywords

AMINE; AZO COMPOUND; CARBAMIC ACID DERIVATIVE; COPPER; COPPER DERIVATIVE; LITHIUM DERIVATIVE; TETRAHYDROFURAN; UREA DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION;

EID: 0033585070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01751-7     Document Type: Article

References (8)

1. Katritzky, A. R.; Pleynet, D. P. M.; Yang, B. J. Org. Chem. 1997, 62, 4155; and references cited therein.
2. Yamaguchi, J.; Hoshi, K.; Takeda, T. Chem. Lett. 1993, 1273.
3. Kurzer, F. Org. Synth. 1963, 49.
4. Kurzer, F. Org. Synth. 1963, 53.
5. Durant, G. J. Chem. Ind. 1965, 1428.
6. Diels, O.; Paquin, M. Chem. Ber. 1913, 46, 2000.
7. Smissman, E. E.; Makriyannis, A. J. Org. Chem. 1973, 38, 1652. 5-Ha: mp 148-149°C (decomp., EtOH). 5-Hb: mp 203-204°C (decomp., EtOH).
8. 4. After removal of the solvent under reduced pressure, the residue was purified by preparative TLC (n-hexane:EtOAc 4:1) and N-(t-butoxycarbonyl)phenethylamine (108 mg) was isolated in 97% yield.