(4S)-4-乙基-4-羟基-1H-吡喃并[3,4-c]吡啶-3,8(4h,7h)-二酮合成路线 （共 48 条）
反应条件
1: 1.) n-BuLi
2: 76 percent / 2 N aq. NaOH / ethanol
3: 1.) TMSCl, NaI, Dabco, 2.) 6 N aq. HCl / 1.) CH3CN, reflux, 5 h, 2.) 100 deg C, 4 h
4: 95 percent / H2, NaOAc / Pd/C / methanol
View Scheme
参考文献
Comins; Baevsky; Hong
Journal of the American Chemical Society, 1992 , vol. 114, # 27 p. 10971 - 10972
反应条件
1: 1.) TMSCl, NaI, Dabco, 2.) 6 N aq. HCl / 1.) CH3CN, reflux, 5 h, 2.) 100 deg C, 4 h
2: 95 percent / H2, NaOAc / Pd/C / methanol
View Scheme
参考文献
Comins; Baevsky; Hong
Journal of the American Chemical Society, 1992 , vol. 114, # 27 p. 10971 - 10972
反应条件
1: 76 percent / 2 N aq. NaOH / ethanol
2: 1.) TMSCl, NaI, Dabco, 2.) 6 N aq. HCl / 1.) CH3CN, reflux, 5 h, 2.) 100 deg C, 4 h
3: 95 percent / H2, NaOAc / Pd/C / methanol
View Scheme
参考文献
Comins; Baevsky; Hong
Journal of the American Chemical Society, 1992 , vol. 114, # 27 p. 10971 - 10972
反应条件
hydrogenchloride; water
T=100°C; 3 h;
参考文献
Yu, Shanbao; Huang, Qing-Qing; Luo, Yu; Lu, Wei
Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 713 - 717
反应条件
hydrogen; palladium dihydroxide in ethanol
T=50°C; 3 h; Title compound not separated from byproducts.;
参考文献
Hiroya, Kou; Kawamoto, Kei; Sakamoto, Takao
Synlett, 2006 , # 16 p. 2636 - 2640
反应条件
hydrogenchloride in water
10 h; Reflux; optical yield given as percent ee;
参考文献
Zhao, Lei; Xiong, Fang-Jun; Chen, Wen-Xue; Chen, Fen-Er
Synthesis, 2011 , # 24 art. no. F87011SS, p. 4045 - 4049
反应条件
1: 5-iodo-4H-1,3-dioxa-8-azanaphthalene With n-butyllithium in tetrahydrofuran
T=-78°C; 0.0833333 h;
2: 2-oxo-butyric acid 2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester in tetrahydrofuran
T=-78 - 20°C; 1 h;
3: With hydrogenchloride in tetrahydrofuran; methanol; isopropyl alcohol
12 h; Heating; Further stages. Title compound not separated from byproducts.;
参考文献
Comins, Daniel L.; Nolan, Jason M.
Organic Letters, 2001 , vol. 3, # 26 p. 4255 - 4257
反应条件
hydrogenchloride
Heating;
参考文献
Fang; Xie; Lowery
Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6142 - 1643
反应条件
1: 42 percent / NaH / CH2Cl2
2: 1.) n-BuLi / tetrahydrofuran / 0.17 h / -10 °C
3: 1.) n-BuLi; 2.) iodine / tetrahydrofuran / 4 h / -23 °C
4: 65 percent / BF3*OEt2 / CH2Cl2
5: 63 percent / n-BuLi / tetrahydrofuran / 0.02 h / -100 °C
6: 75 percent / 10percent HCl / methanol; H2O / 36 h / Heating
7: 95 percent / H2 / Pd/C
View Scheme
参考文献
Comins, Daniel L.; Hong, Hao; Jianhua, Gao
Tetrahedron Letters, 1994 , vol. 35, # 30 p. 5331 - 5334
反应条件
1: 1.) n-BuLi / tetrahydrofuran / 0.17 h / -10 °C
2: 1.) n-BuLi; 2.) iodine / tetrahydrofuran / 4 h / -23 °C
3: 65 percent / BF3*OEt2 / CH2Cl2
4: 63 percent / n-BuLi / tetrahydrofuran / 0.02 h / -100 °C
5: 75 percent / 10percent HCl / methanol; H2O / 36 h / Heating
6: 95 percent / H2 / Pd/C
View Scheme
参考文献
Comins, Daniel L.; Hong, Hao; Jianhua, Gao
Tetrahedron Letters, 1994 , vol. 35, # 30 p. 5331 - 5334
