Protection of a protecting group: Preparation of stable N-silylated t-butyl carbamates

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 191-194

  Roby, Johanne ^a   Voyer, Normand ^a,b  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031021879     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02271-X     Document Type: Article

References (13)

1. Voyer, N.; Roby, J. Tetrahedron Lett., 1995, 36, 6627.
2. For reports on the utility of N-silylated carbamates see: a) Ward, D. E.; Kaller, B. F. Tetrahedron Lett., 1993, 34, 407;
3. b) Radnunz, H.-E.; Reissig, H.-U.; Schneider, G.; Riethmüller, A. Liebigs Ann. Chem., 1990, 705;
4. c) Burkhart, J. P.; Holbert, G. W.; Metcalf, B. W. Tetrahedron Lett. 1984, 25, 5267;
5. d) Adams, J. L.; Chen, T.-M.; Metcalf, B. W. J. Org. Chem 1985, 50, 2730.
6. 3N) to give pure compound.
7. 25=-32° (c=1.2 in MeOH).
8. 2O at -78°C for 3h. After quenching with water and usual work up, the starting material was recovered in more than 92%.
9. Treatment of N-silylated carbamates 1 with TBAF (1 M in THF) leads to N-t-Boc-protected primary amine 2 in quantitative yields in less than 10 min.
10. a) Chang, Y.H.; Chiu, F.T.; Zon, G. J. Org. Chem., 1981, 46, 342.
11. b) Jancke, H.; Engelhardt, G. J. Organometal. Chem., 1977,134, 21.
12. c) Daly, W.H.; Holle, H.J. J. Org. Chem., 1974, 39, 1597.
13. 1, F(000)=666, Scan mode: θ-2θ, θ=2.0 to 143.6°, final R=0.054 for 3159 reflections.