Catalytic hydrogenation of ethyl 2-amino-2-difluoromethyl-4-cyanobutanoate and its Schiff base reaction modes

被引:10
作者
Zhu, JY [1 ]
Price, BA [1 ]
Walker, J [1 ]
Zhao, SX [1 ]
机构
[1] Bristol Myers Squibb Co, Proc Res & Dev, New Brunswick, NJ 08903 USA
关键词
eflornithin; catalytical hydrogenation; catalyst; nitrile reduction;
D O I
10.1016/j.tetlet.2005.02.146
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under heterogeneous catalysis, ethyl 2-amino-2-difluoromethyl-4-cyanobutanoate or its Schiff base could be selectively reduced in good yield by hydrogenation to give a diamine, or to form a five-membered ring or a six-membered ring heterocycles. This selectivity is highly dependent on the type of catalysts used. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2795 / 2797
页数:3
相关论文
共 30 条
[1]   DIRECT SYNTHESIS OF ALPHA-HALOGENOMETHYL-ALPHA-AMINO ACIDS FROM THE PARENT ALPHA-AMINO-ACIDS [J].
BEY, P ;
VEVERT, JP ;
VANDORSSELAER, V ;
KOLB, M .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2732-2742
[2]  
BEY P, 1978, TETRAHEDRON LETT, V52, P5225
[3]   HYDROBORATION .3. THE REDUCTION OF ORGANIC COMPOUNDS BY DIBORANE, AN ACID-TYPE REDUCING AGENT [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) :681-686
[4]   SELECTIVE REDUCTIONS .29. A SIMPLE TECHNIQUE TO ACHIEVE AND ENHANCED RATE OF REDUCTION OF REPRESENTATIVE ORGANIC-COMPOUNDS BY BORANE-DIMETHYL SULFIDE [J].
BROWN, HC ;
CHOI, YM ;
NARASIMHAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3153-3163
[5]   A NEW POWERFUL REDUCING AGENT - SODIUM BOROHYDRIDE IN THE PRESENCE OF ALUMINUM CHLORIDE AND OTHER POLYVALENT METAL HALIDES [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (11) :2582-2588
[6]  
BROWN HC, 1981, SYNTHESIS-STUTTGART, P605
[7]   REVISED STRUCTURE OF BURSATELLIN [J].
CIMINO, G ;
GAVAGNIN, M ;
SODANO, G ;
SPINELLA, A ;
STRAZZULLO, G ;
SCHMITZ, FJ ;
YALAMANCHILI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2301-2303
[8]   PYRROLE CHEMISTRY .26. A SYNTHESIS OF PORPHOBILINOGEN FROM PYRROLE [J].
DEMOPOULOS, BJ ;
ANDERSON, HJ ;
LOADER, CE ;
FABER, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (10) :2415-2422
[9]  
Freifelder M., 1971, PRACTICAL CATALYTIC, P238
[10]  
FREIFELDER M, 1978, CATALYTIC HYDROGENAT, P43