N-(2,2-二甲氧基乙基)-N-2-丙烯-1-基-氨基甲酸苯基甲酯合成路线 （共 6 条）
反应条件
1.1: formic acid / 20 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere 3.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere 3.2: Raney Ni / 4 h / 3102.97 Torr View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50202 A1, 2011 ;
WO 2011/050202 A1
反应条件
1.1: water; formic acid / 20 °C 2.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere 3.1: pentan-1-ol / 20 h / 135 °C 4.1: hydrogen / Raney Ni / ethanol; pentan-1-ol / 4 h / 3102.97 Torr 5.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 0 - 20 °C 7.1: trifluoroacetic acid / dichloromethane / 20 h 7.2: 1.5 h / 60 °C 8.1: ethanol; water / 0.67 h / 20 °C 9.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 1.5 h / 775.74 Torr / Inert atmosphere View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50202 A1, 2011 ;
WO 2011/050202 A1
反应条件
potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in toluene
T=50°C; 48 h; Inert atmosphere;
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50202 A1, 2011 ;
Location in patent: Page/Page column 47 ;
WO 2011/050202 A1
反应条件
1.1: 95 percent / aq. K2CO3 / diethyl ether / 14 h / 20 °C
2.1: NaH / dimethylformamide / 25 °C
2.2: 72 percent / dimethylformamide / 15 h / 20 °C
View Scheme
参考文献
Aggarwal, Varinder K; Roseblade, Stephen; Alexander, Rikki
Organic and biomolecular chemistry, 2003 , vol. 1, # 4 p. 684 - 691
反应条件
1: formic acid / 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere
View Scheme
参考文献
Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry
Patent: US2013/261111 A1, 2013 ;
反应条件
1.1: formic acid / 20 °C / Inert atmosphere
2.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere
3.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere
3.2: Raney Ni / 4 h / 3102.97 Torr
4.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 20 h
6.2: pH ~ 12
7.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50202 A1, 2011 ;
WO 2011/050202 A1
