(-)-5-(3-羟基苯基)-2-甲基吗吩烷合成路线 （共 8 条）
反应条件
1.1: aq. H3PO4; formic acid / 72 h / 20 °C
2.1: 35.2 g / NaBH4 / methanol / 2 h / 20 °C
3.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h
3.2: NH4OH
4.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr
5.1: hydrogen / Pd/C
6.1: aq. HBr
View Scheme
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
反应条件
1.1: n-BuLi / tetrahydrofuran / 2 h / -60 °C
1.2: tetrahydrofuran / 2 h / 20 °C
2.1: 51.4 g / p-toluenesulfonic acid monohydrate / toluene / 6 h / Heating
3.1: sec-BuLi / cyclohexane; tetrahydrofuran / 1 h / -40 °C
3.2: cyclohexane; tetrahydrofuran / 2 h / 0 °C
4.1: aq. H3PO4; formic acid / 72 h / 20 °C
5.1: 35.2 g / NaBH4 / methanol / 2 h / 20 °C
6.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h
6.2: NH4OH
7.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr
8.1: hydrogen / Pd/C
9.1: aq. HBr
View Scheme
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
反应条件
1.1: n-BuLi / tetrahydrofuran / 2 h / -60 °C
1.2: tetrahydrofuran / 2 h / 20 °C
2.1: 51.4 g / p-toluenesulfonic acid monohydrate / toluene / 6 h / Heating
3.1: sec-BuLi / cyclohexane; tetrahydrofuran / 1 h / -40 °C
3.2: cyclohexane; tetrahydrofuran / 2 h / 0 °C
4.1: aq. H3PO4; formic acid / 72 h / 20 °C
5.1: 35.2 g / NaBH4 / methanol / 2 h / 20 °C
6.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h
6.2: NH4OH
7.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr
8.1: hydrogen / Pd/C
9.1: aq. HBr
View Scheme
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
反应条件
1.1: 51.4 g / p-toluenesulfonic acid monohydrate / toluene / 6 h / Heating
2.1: sec-BuLi / cyclohexane; tetrahydrofuran / 1 h / -40 °C
2.2: cyclohexane; tetrahydrofuran / 2 h / 0 °C
3.1: aq. H3PO4; formic acid / 72 h / 20 °C
4.1: 35.2 g / NaBH4 / methanol / 2 h / 20 °C
5.1: (+)-di-O,O'-p-toluyl-D-tartaric acid / acetone / 0.33 h
5.2: NH4OH
6.1: 93 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C / 3102.97 Torr
7.1: hydrogen / Pd/C
8.1: aq. HBr
View Scheme
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
反应条件
1: BBr3 / CHCl3 / 0.25 h / Ambient temperature
2: resolution of the racemate via salt with (-)-O,O'-dibenzoyl-L-tartaric acid
3: HCl (g), Zn / diethyl ether
View Scheme
参考文献
Bertha, Craig M.; Mattson, Mariena V.; Flippen-Anderson, Judith L.; Rothman, Richard B.; Xu, Heng; et al.
Journal of Medicinal Chemistry, 1994 , vol. 37, # 19 p. 3163 - 3170
反应条件
1: resolution of the racemate via salt with (-)-O,O'-dibenzoyl-L-tartaric acid
2: HCl (g), Zn / diethyl ether
View Scheme
参考文献
Bertha, Craig M.; Mattson, Mariena V.; Flippen-Anderson, Judith L.; Rothman, Richard B.; Xu, Heng; et al.
Journal of Medicinal Chemistry, 1994 , vol. 37, # 19 p. 3163 - 3170
反应条件
1: hydrogen / Pd/C
2: aq. HBr
View Scheme
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
参考文献
Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.
Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1177 - 1190
