Selective removal of the N-BOC protective group using silica gel at low pressure

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1471-1472

  Apelqvist, Theresa ^a   Wensbo, David ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029874190     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02398-4     Document Type: Article

References (8)

1. Greene, T.W.; Wuts, P.G.M. In Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1991.
2. Stafford, J.A.; Brackeen, M.F.; Karanewsky, D.S.; Valvano N.L. Tetrahedron Lett. 1993, 34, 7873-7876.
3. Wensbo, D.; Annby, U.; Gronowitz, S.Tetrahedron 1995, 51, 10323-10342.
4. Rawal, V.; Cava, M. Tetrahedron Lett. 1985, 26, 6141-6142. See citations in ref. 3 for the use of this procedure in the deprotection of indoles and other nitrogen protected compounds.
5. For a recent report on removal of N-BOC groups in amino acid tert-butyl esters see: Gibson, F.S.; Bergmeier, S.C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216-3218.
6. The silica gel was kept at 50°C / 0.2 mmHg for 24 h before use.
7. Prepared by refluxing 20g of silica gel (35-70 Mesh) in a mixture of 50ml of HMDS, 1ml of TMSCl and 0.5g of ammonium sulphate for 96h, followed by evaporation of the solvent and drying at 0.2 mmHg.
8. Mehta, A.; Jaouhari, R.; Benson, T.J.; Douglas K.T. Tetrahedron Lett. 1992, 33, 5441-5444 and references cited therein.