5-(氯甲基)-2,3-二氢-1H-茚合成路线 （共 19 条）
反应条件
ethanol; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane
参考文献
Arnold
Journal of the American Chemical Society, 1939 , vol. 61, p. 1405
反应条件
1: 166.8 mg / sodium azide / dimethylformamide / 22 h / 70 °C 2: 86 percent / lithium aluminum hydride / tetrahydrofuran / -78 - 0 °C View Scheme
参考文献
Michelotti, Enrique L.; Moffett, Kristofer K.; Nguyen, Duyan; Kelly, Martha J.; Shetty, Rupa; Chai, Xiaomei; Northrop, Katrina; Namboodiri, Variketta; Campbell, Brandon; Flynn, Gary A.; Fujimoto, Ted; Hollinger, Frank P.; Bukhtiyarova, Marina; Springman, Eric B.; Karpusas, Michael
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5274 - 5279
反应条件
1.) 5 min, reflux, methanol; 2.) 5 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Neudeck, Horst K.
Monatshefte fuer Chemie, 1988 , vol. 119, p. 625 - 644
反应条件
thionyl chloride in chloroform
T=0 - 20°C; 12 h;
参考文献
VERTEX PHARMACEUTICALS INCORPORATED
Patent: WO2008/141119 A2, 2008 ;
Location in patent: Page/Page column 73-74 ;
WO 2008/141119 A2
反应条件
hydrogenchloride in tetrachloromethane
1 h;
参考文献
Billups, W. E.; Rodin, Wayne A.
Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1312 - 1314
反应条件
hydrogenchloride; acetic acid; paraformaldehyde
参考文献
American Home Products Corporation
Patent: US4895860 A1, 1990 ;
反应条件
hydrogenchloride in benzene
1.5 h; Ambient temperature;
参考文献
Ellingboe; Alessi; Dolak; Nguyen; Tomer; Guzzo; Bagli; McCaleb
Journal of Medicinal Chemistry, 1992 , vol. 35, # 7 p. 1176 - 1183
反应条件
1.1: aq. hydrobromic acid; sodium nitrite / 0.33 h / 0 - 5 °C
1.2: 42 percent / copper(I) bromide; aq. hydrobromic acid / 0.67 h / 60 °C
2.1: tert-butyllithium / diethyl ether; pentane / 1 h / -70 °C
2.2: diethyl ether / 1 h / -70 - 10 °C
3.1: 23.1 g / sodium borohydride / ethanol / 1.5 h / 0 - 20 °C
4.1: thionyl bromide / CH2Cl2 / 1 h / 20 °C
5.1: 3.79 g / aq. sodium sulfite; tetra-n-butylammonium bromide / acetone / 2 h / Heating
6.1: 12 h / 120 °C
6.2: thionyl chloride / 20 °C
View Scheme
参考文献
Michelotti, Enrique L.; Moffett, Kristofer K.; Nguyen, Duyan; Kelly, Martha J.; Shetty, Rupa; Chai, Xiaomei; Northrop, Katrina; Namboodiri, Variketta; Campbell, Brandon; Flynn, Gary A.; Fujimoto, Ted; Hollinger, Frank P.; Bukhtiyarova, Marina; Springman, Eric B.; Karpusas, Michael
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5274 - 5279
反应条件
1.1: tert-butyllithium / diethyl ether; pentane / 1 h / -70 °C
1.2: diethyl ether / 1 h / -70 - 10 °C
2.1: 23.1 g / sodium borohydride / ethanol / 1.5 h / 0 - 20 °C
3.1: thionyl bromide / CH2Cl2 / 1 h / 20 °C
4.1: 3.79 g / aq. sodium sulfite; tetra-n-butylammonium bromide / acetone / 2 h / Heating
5.1: 12 h / 120 °C
5.2: thionyl chloride / 20 °C
View Scheme
参考文献
Michelotti, Enrique L.; Moffett, Kristofer K.; Nguyen, Duyan; Kelly, Martha J.; Shetty, Rupa; Chai, Xiaomei; Northrop, Katrina; Namboodiri, Variketta; Campbell, Brandon; Flynn, Gary A.; Fujimoto, Ted; Hollinger, Frank P.; Bukhtiyarova, Marina; Springman, Eric B.; Karpusas, Michael
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5274 - 5279
反应条件
1.1: 3.79 g / aq. sodium sulfite; tetra-n-butylammonium bromide / acetone / 2 h / Heating
2.1: 12 h / 120 °C
2.2: thionyl chloride / 20 °C
View Scheme
参考文献
Michelotti, Enrique L.; Moffett, Kristofer K.; Nguyen, Duyan; Kelly, Martha J.; Shetty, Rupa; Chai, Xiaomei; Northrop, Katrina; Namboodiri, Variketta; Campbell, Brandon; Flynn, Gary A.; Fujimoto, Ted; Hollinger, Frank P.; Bukhtiyarova, Marina; Springman, Eric B.; Karpusas, Michael
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5274 - 5279
