(1R,4S)-2-氧代-7-氮杂双环[2.2.1]庚烷-7-羧酸叔丁酯合成路线 （共 72 条）
反应条件
acetic acid in methanol T=40°C; 18 h;
参考文献
Dallanoce, Clelia; Matera, Carlo; De Amici, Marco; Rizzi, Luca; Pucci, Luca; Gotti, Cecilia; Clementi, Francesco; De Micheli, Carlo
Chirality, 2012 , vol. 24, # 7 p. 543 - 551
参考文献
Tachihara, Toru; Watanabe, Hiroyuki; Kitahara, Takeshi
Heterocycles, 2002 , vol. 57, # 5 p. 781 - 785
反应条件
1: NaBH4 / methanol / 0.5 h / Ambient temperature 2: Et3N / CH2Cl2 3: 77 percent / NaN3 / dimethylformamide / 24 h / 80 °C 4: 98 percent / 5percent HCl / methanol / 0.25 h / Ambient temperature 5: 1.) SOCl2, Et3N, 2.) NaIO4, RuCl3 / 1.) CH2Cl2, room temperature, 15 min, 2.) CCl4, CH3CN, H2O, room temperature, 1 h 6: 82 percent / H2 / Pd/C / tetrahydrofuran; H2O / 2 h / 1551.4 Torr 7: conc. H2SO4, H2O / tetrahydrofuran / 1 h / Heating 8: K2CO3 / CH2Cl2 / 18 h / Ambient temperature 9: 85 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -70 - 20 °C View Scheme
参考文献
Tetrahedron, , vol. 53, # 50 p. 17177 - 17194
反应条件
1: 1.) SOCl2, Et3N, 2.) NaIO4, RuCl3 / 1.) CH2Cl2, room temperature, 15 min, 2.) CCl4, CH3CN, H2O, room temperature, 1 h 2: 82 percent / H2 / Pd/C / tetrahydrofuran; H2O / 2 h / 1551.4 Torr 3: conc. H2SO4, H2O / tetrahydrofuran / 1 h / Heating 4: K2CO3 / CH2Cl2 / 18 h / Ambient temperature 5: 85 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -70 - 20 °C View Scheme
参考文献
Tetrahedron, , vol. 53, # 50 p. 17177 - 17194
反应条件
1: 98 percent / 5percent HCl / methanol / 0.25 h / Ambient temperature 2: 1.) SOCl2, Et3N, 2.) NaIO4, RuCl3 / 1.) CH2Cl2, room temperature, 15 min, 2.) CCl4, CH3CN, H2O, room temperature, 1 h 3: 82 percent / H2 / Pd/C / tetrahydrofuran; H2O / 2 h / 1551.4 Torr 4: conc. H2SO4, H2O / tetrahydrofuran / 1 h / Heating 5: K2CO3 / CH2Cl2 / 18 h / Ambient temperature 6: 85 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -70 - 20 °C View Scheme
参考文献
Tetrahedron, , vol. 53, # 50 p. 17177 - 17194
反应条件
1: 82 percent / H2 / Pd/C / tetrahydrofuran; H2O / 2 h / 1551.4 Torr 2: conc. H2SO4, H2O / tetrahydrofuran / 1 h / Heating 3: K2CO3 / CH2Cl2 / 18 h / Ambient temperature 4: 85 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -70 - 20 °C View Scheme
参考文献
Tetrahedron, , vol. 53, # 50 p. 17177 - 17194
反应条件
2: 98 percent / H2, DIEA / Pd/C / methanol / 5 h View Scheme
参考文献
Journal of Organic Chemistry, , vol. 61, # 18 p. 6313 - 6325
反应条件
1: 100 percent / TFA / CH2Cl2 / 48 h 3: 98 percent / H2, DIEA / Pd/C / methanol / 5 h View Scheme
参考文献
Journal of Organic Chemistry, , vol. 61, # 18 p. 6313 - 6325
反应条件
1: 66 percent / Cs2CO3 / dimethylformamide / 40 h / 70 °C 2: 80percent m-CPBA / CH2Cl2 / 4 h / Ambient temperature 3: 78 percent / aq. K2CO3 / methanol / 72 h / Ambient temperature 4: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 °C 5: 5 N HCl, H2 / Pd(OH)2/C / ethanol / 6 h / 40 °C / 2068.6 Torr 6: 1 N NaOH / dioxane / 18 h / Ambient temperature 7: 42 percent / DMAP / CH2Cl2 / 18 h / Ambient temperature 8: 85 percent / KOH / ethanol / 2 h / Ambient temperature 9: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min View Scheme
参考文献
Journal of Organic Chemistry, , vol. 59, # 7 p. 1771 - 1778
反应条件
1: 80percent m-CPBA / CH2Cl2 / 4 h / Ambient temperature 2: 78 percent / aq. K2CO3 / methanol / 72 h / Ambient temperature 3: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 °C 4: 5 N HCl, H2 / Pd(OH)2/C / ethanol / 6 h / 40 °C / 2068.6 Torr 5: 1 N NaOH / dioxane / 18 h / Ambient temperature 6: 42 percent / DMAP / CH2Cl2 / 18 h / Ambient temperature 7: 85 percent / KOH / ethanol / 2 h / Ambient temperature 8: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min View Scheme
参考文献
Journal of Organic Chemistry, , vol. 59, # 7 p. 1771 - 1778
