Reductive amination with zinc borohydride. Efficient, safe route to fluorinated benzylamines

被引:53
作者
Bhattacharyya, S [1 ]
Chatterjee, A [1 ]
Williamson, JS [1 ]
机构
[1] UNIV MISSISSIPPI,SCH PHARM,DEPT MED CHEM,UNIVERSITY,MS 38677
关键词
D O I
10.1080/00397919708005050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluorinated benzylamines are synthesized in high yields by reductive alkylation of secondary amines with appropriate fluoroaldehydes using a combination of zinc chloride and zinc borohydride. The present method offers an alternative to toxic sodium cyanoborohydride and is adaptable to multigram-scale preparations.
引用
收藏
页码:4265 / 4274
页数:10
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共 68 条
[31]  
Kirschbaum J., 1983, ANAL PROFILES DRUG S, V12, P1
[32]   DESIGN AND SYNTHESIS OF NEW FLUORINATED FERROELECTRIC LIQUID-CRYSTALLINE POLYMERS [J].
KITAZUME, T ;
OHNOGI, T ;
ITO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6608-6615
[33]  
Kukhar V. P., 1993, RUSS CHEM REV, V62, P284
[34]  
Kukhar VP, 1994, FLUORINE CONTAINING
[35]  
LANE CF, 1975, SYNTHESIS-STUTTGART, P135
[36]  
Lenga R. E., 1985, SIGMA ALDRICH LIB CH, P1609
[37]  
MAIN BG, 1993, MED CHEM, P187
[38]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF METABOLITES OF RIMANTADINE [J].
MANCHAND, PS ;
CERRUTI, RL ;
MARTIN, JA ;
HILL, CH ;
MERRETT, JH ;
KEECH, E ;
BELSHE, RB ;
CONNELL, EV ;
SIM, IS .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (07) :1992-1995
[39]   REDUCTIVE AMINATION OF PIPERIDINES WITH ALDEHYDES USING BORANE-PYRIDINE [J].
MOORMANN, AE .
SYNTHETIC COMMUNICATIONS, 1993, 23 (06) :789-795
[40]   NEW AND EFFECTIVE ROUTES TO FLUORO ANALOGS OF ALIPHATIC AND AROMATIC AMINO-ACIDS [J].
OJIMA, I ;
KATO, K ;
NAKAHASHI, K ;
FUCHIKAMI, T ;
FUJITA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4511-4522