N-甲氧基-N-甲基苯甲酰胺合成路线 （共 140 条）
反应条件
1: 2-picoline With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; Inert atmosphere; 2: N-Methoxy-N-methyl-benzamide in tetrahydrofuran; hexane T=-78°C; 3 h; Inert atmosphere;
参考文献
Muir, Calum W.; Kennedy, Alan R.; Redmond, Joanna M.; Watson, Allan J. B.
Organic and Biomolecular Chemistry, 2013 , vol. 11, # 20 p. 3337 - 3340
反应条件
1: 4-methoxy-benzaldehyde With TMSC(Li)N2 in tetrahydrofuran; hexane
T=-78 - 20°C; 1.5 h;
2: With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.5 h;
3: N-Methoxy-N-methyl-benzamide in tetrahydrofuran; hexane
T=20°C; 1 h; Further stages.;
参考文献
Hari, Yoshiyuki; Date, Koji; Aoyama, Toyohiko
Heterocycles, 2007 , vol. 74, # C p. 545 - 552
反应条件
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 0 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Tinarelli, Alessandro; Righi, Paolo; Rosini, Goffredo; Andreotti, Daniele; Profeta, Roberto; Spada, Simone
Tetrahedron, 2011 , vol. 67, # 3 p. 612 - 617
反应条件
1: 1.) t-BuLi / 1.) THF, pentane, -40 deg C, 1 h, 2.) THF, pentane, 20 deg C, 1 h
2: 5.5 M HCl / 1 h / 45 - 50 °C
View Scheme
参考文献
Hands, David; Bishop, Brian; Cameron, Mark; Edwards, John S.; Cottrell, Ian F.; Wright, Stanley H. B.
Synthesis, 1996 , # 7 p. 877 - 882
反应条件
2,2,6,6-tetramethylpiperidinyl-lithium
1) THF, hexane, -78 deg C, 20 min, 2) THF, -78 deg C, 1.5 h; Yield given. Multistep reaction;
参考文献
Ward, John S.; Merritt, Leander
Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 3 p. 765 - 768
反应条件
2: 99 percent / NEt(i-Pr)2 / tetrahydrofuran / Ambient temperature
View Scheme
参考文献
Bromidge; Entwistle; Goldstein; Orlek
Synthetic Communications, 1993 , vol. 23, # 4 p. 487 - 494
反应条件
1: 4-Methylpyridine With lithium diisopropyl amide in tetrahydrofuran; cyclohexane
T=-78 - 0°C; 0.5 h;
2: N-Methoxy-N-methyl-benzamide in tetrahydrofuran; cyclohexane
T=-78 - 20°C;
参考文献
ALLERGAN, INC.
Patent: WO2009/91760 A1, 2009 ;
Location in patent: Page/Page column 37 ;
WO 2009/091760 A1
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.42 h / -78 °C / Inert atmosphere
1.2: 20 h / -78 - 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Shintani, Ryo; Ito, Tomoaki; Hayashi, Tamio
Organic Letters, 2012 , vol. 14, # 9 p. 2410 - 2413
反应条件
1: N-Methoxy-N-methyl-benzamide; 2-propen-2-ylmagnesium bromide in tetrahydrofuran
T=0 - 20°C; 1.16667 h;
2: morpholine in tetrahydrofuran; water
T=20°C; 0.333333 h; Further stages.;
参考文献
Gomtsyan; Koenig; Lee
Journal of Organic Chemistry, 2001 , vol. 66, # 10 p. 3613 - 3616
反应条件
1: With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in hexanes
T=-20°C; 0.333333 h;
2: methyl 4-(trifluoromethyl)phenyl ether in tetrahydrofuran; hexanes
T=-20°C; 0.25 h;
3: N-Methoxy-N-methyl-benzamide in tetrahydrofuran; hexanes
T=-20°C; 0.166667 h;
参考文献
ELI LILLY AND COMPANY
Patent: WO2005/19151 A1, 2005 ;
Location in patent: Page/Page column 127 ;
WO 2005/019151 A1
