(3S,4r)-1-boc-3-羟基甲基-4-(4-氟苯基)-哌啶合成路线 （共 32 条）
反应条件
1: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr
2: sodium methoxide / toluene; methanol / 1 h / 75 °C
3: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C
4: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C
View Scheme
参考文献
Taylor, Mark S.; Jacobsen, Eric N.
Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11204 - 11205
反应条件
1: Et3N / tetrahydrofuran / 0.17 h / 20 °C
2: KOt-Bu / tetrahydrofuran / 0.5 h / 0 °C
3: 0.327 g / TBAF / tetrahydrofuran / 12 h
View Scheme
参考文献
Johnson; Curtis; Beak
Journal of the American Chemical Society, 2001 , vol. 123, # 5 p. 1004 - 1005
反应条件
sodium methylate in methanol
T=0°C; 1 h;
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
反应条件
1: MeONa / methanol / 1 h / 0 °C
2: 80 percent / H2 / Pd/C / ethanol / 48 h
3: Na2CO3 / CH2Cl2; H2O / 1 h / 0 °C
View Scheme
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
反应条件
1: MeONa / methanol / 1 h / 0 °C
2: 88 percent / H2 / Pd/C / ethanol / 24 h
3: Na2CO3 / CH2Cl2; H2O / 1 h / 0 °C
View Scheme
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
反应条件
1: With sodium carbonate in dichloromethane; water
T=0°C; 1 h;
2: With Candida antarctica B; benzoic acid vinyl ester in toluene
T=30°C; 7 h; Enzymatic reaction; Further stages.;
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
反应条件
1.1: NaOMe / methanol / 3 h / 63 - 66 °C
2.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr
3.1: NaOMe / toluene / 0.5 h / 70 - 80 °C
4.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C
4.2: via salt with L-o-chlorotartranilic acid/Celite
5.1: aq. NaOH / toluene / 2 h / 45 - 55 °C
View Scheme
参考文献
Sugi, Kiyoshi; Itaya, Nobushige; Katsura, Tadashi; Igi, Masami; Yamazaki, Shigeya; Ishibashi, Taro; Yamaoka, Teiji; Kawada, Yoshihiro; Tagami, Yayoi; Otsuki, Michiya; Ohshima, Takao
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 4 p. 529 - 536
反应条件
1.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr
2.1: NaOMe / toluene / 0.5 h / 70 - 80 °C
3.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C
3.2: via salt with L-o-chlorotartranilic acid/Celite
4.1: aq. NaOH / toluene / 2 h / 45 - 55 °C
View Scheme
参考文献
Sugi, Kiyoshi; Itaya, Nobushige; Katsura, Tadashi; Igi, Masami; Yamazaki, Shigeya; Ishibashi, Taro; Yamaoka, Teiji; Kawada, Yoshihiro; Tagami, Yayoi; Otsuki, Michiya; Ohshima, Takao
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 4 p. 529 - 536
反应条件
1: Na2CO3 / CH2Cl2; H2O / 1 h / 0 °C
2: Candida antarctica lipase A / toluene / 5 h / 15 °C / Enzymatic reaction
3: MeONa / methanol / 1 h / 0 °C
View Scheme
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
反应条件
1: 64 percent / KOH / toluene / 24 h / Heating
2: Na2CO3 / CH2Cl2; H2O / 1 h / 0 °C
View Scheme
参考文献
De Gonzalo; Brieva; Sanchez; Bayod; Gotor
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8947 - 8953
