5-氯螺[3H-苯并呋喃-2,4'-哌啶]合成路线 (共 8 条)
反应条件
hydrogenchloride in tetrahydrofuran
T=20 - 50°C; 22 h;
参考文献
ASTRAZENECA AB
Patent: WO2005/54249 A1, 2005 ;
Location in patent: Page/Page column 20-21 ;
WO 2005/054249 A1
反应条件
1: 1.) Mg / 1.) iodine / 1.) ether, reflux, 20 h; 2.) ether, r.t., 2 h
2: 81 percent / 50percent sodium hydride (oil dispersion) / benzene; dimethylformamide / 4 h / Heating
3: 1.) ethyl chloroformate; 2.) 50percent KOH / 1.) benzene, reflux, 24 h; 2.) ethanol, reflux, 18 h
View Scheme
参考文献
Effland, Richard C.; Gardner, Beth Ann; Strupczewski, Joseph
Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 811 - 814
反应条件
1: 1.) Mg / 1.) iodine / 1.) ether, reflux, 20 h; 2.) ether, r.t., 2 h
2: 81 percent / 50percent sodium hydride (oil dispersion) / benzene; dimethylformamide / 4 h / Heating
3: 1.) ethyl chloroformate; 2.) 50percent KOH / 1.) benzene, reflux, 24 h; 2.) ethanol, reflux, 18 h
View Scheme
参考文献
Effland, Richard C.; Gardner, Beth Ann; Strupczewski, Joseph
Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 811 - 814
反应条件
1: 81 percent / 50percent sodium hydride (oil dispersion) / benzene; dimethylformamide / 4 h / Heating
2: 1.) ethyl chloroformate; 2.) 50percent KOH / 1.) benzene, reflux, 24 h; 2.) ethanol, reflux, 18 h
View Scheme
参考文献
Effland, Richard C.; Gardner, Beth Ann; Strupczewski, Joseph
Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 811 - 814
反应条件
1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 °C
1.2: 18 h / 40 °C
2.1: potassium tert-butylate / 40 h / 40 - 50 °C
3.1: hydrogenchloride / tetrahydrofuran
View Scheme
参考文献
Hossain, Nafizal; Ivanova, Svetlana; Bergare, Jonas; Eriksson, Tomas
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 6 p. 1883 - 1886
反应条件
1: potassium tert-butylate / 40 h / 40 - 50 °C
2: hydrogenchloride / tetrahydrofuran
View Scheme
参考文献
Hossain, Nafizal; Ivanova, Svetlana; Bergare, Jonas; Eriksson, Tomas
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 6 p. 1883 - 1886
反应条件
1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 °C
1.2: 18 h / 40 °C
2.1: potassium tert-butylate / 40 h / 40 - 50 °C
3.1: hydrogenchloride / tetrahydrofuran
View Scheme
参考文献
Hossain, Nafizal; Ivanova, Svetlana; Bergare, Jonas; Eriksson, Tomas
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 6 p. 1883 - 1886
反应条件
potassium hydroxide; chloroformic acid ethyl ester
1.) benzene, reflux, 24 h; 2.) ethanol, reflux, 18 h; Yield given. Multistep reaction;
参考文献
Effland, Richard C.; Gardner, Beth Ann; Strupczewski, Joseph
Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 811 - 814