Large-scale oxidations in the pharmaceutical industry

被引:732
作者
Caron, Stephane [1 ]
Dugger, Robert W. [1 ]
Ruggeri, Sally Gut [1 ]
Ragan, John A. [1 ]
Ripin, David H. Brown [1 ]
机构
[1] Pfizer Inc, Chem Res & Dev, Pfizer Global Res Div, Groton, CT 06340 USA
关键词
D O I
10.1021/cr040679f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidation reactions are powerful tools to convert a position that is protected in a lower oxidation state to the desired functionality and for the functionalization of otherwise unfunctionalized positions. Despite their power as a synthetic tool, these reactions are not fully utilized in the pharmaceutical industry. To illustrate the reasons for this hesitation, an overview is given of the currently acceptable methods for large-scale oxidations of alkenes, arenes, alkylarenes, alcohols, amines, sulfides, and other substrates. It is shown that the Moffat oxidation and TEMPO-based oxidants are especially valuable for the conversion of primary alcohols into aldehydes.
引用
收藏
页码:2943 / 2989
页数:47
相关论文
共 375 条
[61]   A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide-urea complex [J].
Caron, S ;
Do, NM ;
Sieser, JE .
TETRAHEDRON LETTERS, 2000, 41 (14) :2299-2302
[62]   Process development and scale-up of the potential thiazolidinedione antidiabetic candidate PNU-91325 [J].
Carpenter, DE ;
Imbordino, RJ ;
Maloney, MT ;
Moeslein, JA ;
Reeder, MR ;
Scott, A .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (05) :721-728
[63]   Synthetic studies toward the partial ergot alkaloid LY228729, a potent 5HT(1A) receptor agonist [J].
Carr, MA ;
Creviston, PE ;
Hutchison, DR ;
Kennedy, JH ;
Khau, VV ;
Kress, TJ ;
Leanna, MR ;
Marshall, JD ;
Martinelli, MJ ;
Peterson, BC ;
Varie, DL ;
Wepsiec, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8640-8653
[64]  
Caskey D. C., 1990, [No title captured], Patent No. [WO 9010617, 9010617]
[65]  
CHALK AJ, 1993, Patent No. 553668
[66]   The synthesis of gem-cyclopentyl substituted glutarates via the oxidative ring contraction of 2-acetylcyclohexanones [J].
Challenger, S ;
Derrick, A ;
Silk, TV .
SYNTHETIC COMMUNICATIONS, 2002, 32 (19) :2911-2918
[67]  
CHAPMAN RC, 1988, Patent No. 254432
[68]  
CHEN BC, 2002, Patent No. 2002024638
[69]  
Chen R. H. K., 1993, U. S. Patent, Patent No. [5,208,327, 5208327]
[70]  
CHIU FT, 2001, Patent No. 6177567