(1S,2S,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯合成路线 （共 10 条）
反应条件
in methanol; diethyl ether Methylation;
参考文献
Qiu, Jian; Silverman, Richard B.
Journal of Medicinal Chemistry, 2000 , vol. 43, # 4 p. 706 - 720
反应条件
1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 3.1: triethylamine / methanol / 5 - 20 °C 4.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 5.1: KOAc / dimethylformamide / 72 h / 60 °C 5.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Qiu, Jian; Silverman, Richard B.
Journal of Medicinal Chemistry, 2000 , vol. 43, # 4 p. 706 - 720
反应条件
1.1: N-bromosuccinimide / tetrahydrofuran; H2O / 17 h / 20 °C 2.1: KOH / H2O; methanol / 48 h / 90 °C 2.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 3.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 4.1: triethylamine / methanol / 5 - 20 °C 5.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 6.1: KOAc / dimethylformamide / 72 h / 60 °C 6.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 2.1: triethylamine / methanol / 5 - 20 °C 3.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 4.1: KOAc / dimethylformamide / 72 h / 60 °C 4.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 3.1: triethylamine / methanol / 5 - 20 °C 4.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 5.1: KOAc / dimethylformamide / 72 h / 60 °C 5.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Lloyd, Richard C.; Lloyd, Michael C.; Smith, Mark E. B.; Holt, Karen E.; Swift, Jonathan P.; Keene, Philip A.; Taylor, Stephen J. C.; McCague, Raymond
Tetrahedron, 2004 , vol. 60, # 3 p. 717 - 728
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 6.1: NEt3 / methanol / 5 - 20 °C 7.1: TEA; DMAP / CH2Cl2 / 5 °C 8.1: dimethylformamide / 60 °C 9.1: NaOMe / methanol / 5 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: lactamase / Enzymatic reaction 2.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 3.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 4.1: NBS / tetrahydrofuran; H2O / 20 °C 5.1: KOH / methanol; H2O / 90 °C 5.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 6.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 7.1: NEt3 / methanol / 5 - 20 °C 8.1: TEA; DMAP / CH2Cl2 / 5 °C 9.1: dimethylformamide / 60 °C 10.1: NaOMe / methanol / 5 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1: 94 percent / aq. K2CO3 / methanol / 4 h 2: 95 percent / methanol; diethyl ether View Scheme
参考文献
Qiu, Jian; Silverman, Richard B.
Journal of Medicinal Chemistry, 2000 , vol. 43, # 4 p. 706 - 720
反应条件
1.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 2.1: KOAc / dimethylformamide / 72 h / 60 °C 2.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: triethylamine / methanol / 5 - 20 °C 2.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 3.1: KOAc / dimethylformamide / 72 h / 60 °C 3.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
