Montmorillonite K 10 and montmorillonite KSF as new and reusable catalysts for conversion of arnines to N-tert-butylcarbamates

被引:70
作者
Chankeshwara, Sunay V. [1 ]
Chakraborti, Asit K. [1 ]
机构
[1] NIPER, Dept Med Chem, Nagar 160062, Punjab, India
关键词
montmorillonite K 10; montmorillonite KSF; catalyst; N-tert-butylcarbamates; amines; chiral alpha-amino acid esters; di-tert-butyl dicarbonate; chemoselective; solvent-free; room temperature;
D O I
10.1016/j.molcata.2006.03.042
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Montmorillonite K 10 and montmorillonite KSF were found to be new and reusable catalysts for chemoselective conversion of an-lines to N-t-Boc derivatives at room temperature under solvent-free conditions without competitive formation of isocyanate, urea and N,N-di-t-Boc. Various aromatic, heteroaromatic and aliphatic amines afforded N-t-butylcarbamates in excellent yields on treatment with (Boc)(2)O after 5 min-2 h. Chiral amine and esters of a-amino acids afforded optically pure N-t-Boc derivatives in high yields. The catalytic efficiency of montmorillonite KSF was marginally inferior to that of montmorillonite K 10. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:198 / 202
页数:5
相关论文
共 57 条
[1]   The reactivity of the N-Boc protecting group:: an underrated feature [J].
Agami, C ;
Couty, F .
TETRAHEDRON, 2002, 58 (14) :2701-2724
[2]  
[Anonymous], 2005, ALDRICH ADV SCI, P514
[3]  
[Anonymous], 2003, ALDRICH HDB FINE CHE, P336
[4]   Synthesis of syn- and anti-1,2-amino alcohols by regioselective ring opening reactions of cis-3-aminooxetanes [J].
Bach, T ;
Schroder, J .
TETRAHEDRON LETTERS, 1997, 38 (21) :3707-3710
[5]  
BARCELO G, 1986, SYNTHESIS-STUTTGART, P627
[6]   A Lewis acid-mediated protocol for the protection of aryl amines as their Boc-derivatives [J].
Bartoli, G ;
Bosco, M ;
Locatelli, M ;
Marcantoni, E ;
Massaccesi, M ;
Melchiorre, P ;
Sambri, L .
SYNLETT, 2004, (10) :1794-1798
[7]   Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited.: Their reactions with amines and alcohols [J].
Basel, Y ;
Hassner, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6368-6380
[8]   Facile inversion of configuration of N-Boc-β-aminoalcohols via SN2 cyclization to oxazolidinones [J].
Benedetti, F ;
Norbedo, S .
TETRAHEDRON LETTERS, 2000, 41 (51) :10071-10074
[9]   A mild amide to carbamate transformation [J].
Burk, MJ ;
Allen, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7054-7057
[10]   Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].
Cave, GWV ;
Raston, CL ;
Scott, JL .
CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169