(1S,3S,5S)-3-(氨基羰基)-2-氮杂双环[3.1.0]己烷-2-甲酸叔丁酯合成路线 （共 11 条）
反应条件
1: With 4-methyl-morpholine; isobutyl chloroformate in tetrahydrofuran T=-15°C; 0.5 h; 2: With ammonia in tetrahydrofuran; 1,4-dioxane T=-30 - 20°C;
参考文献
ALANTOS PHARMACEUTICALS, INC.
Patent: WO2006/116157 A2, 2006 ;
Location in patent: Page/Page column 114-116 ;
WO 2006/116157 A2
反应条件
1: diiodomethane With diethylzinc in ethylene glycol dimethyl ether; dichloromethane; toluene T=-30 - -25°C; Simmons-Smith Reaction; 0.75 h; 2: BMS-562419 in ethylene glycol dimethyl ether; dichloromethane; toluene T=22 - 24°C; 3: With sodium hydrogencarbonate in ethylene glycol dimethyl ether; dichloromethane; water; toluene T=15°C; 1 h;
参考文献
Sharma, Padam N.; Galvin, Gabriel M.; Boettger, Susan D.; Racha, Saibaba; Zhu, Jingyang; Melton, Jack; Mudryk, Boguslaw M.
Patent: US2006/35954 A1, 2006 ;
Location in patent: Page/Page column 6-7 ;
反应条件
1: 4-(N,N-dimethlyamino)pyridine 2: lithium triethylborohydride / toluene / -70 - -60 °C 3: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 4: water; lithium hydroxide hydrate / ethanol 5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 6: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 22, # 4 p. 1383 - 1393
反应条件
1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 2: water; lithium hydroxide hydrate / ethanol 3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 4: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 22, # 4 p. 1383 - 1393
反应条件
1: lithium triethylborohydride / toluene / -70 - -60 °C 2: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 3: water; lithium hydroxide hydrate / ethanol 4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 5: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 22, # 4 p. 1383 - 1393
反应条件
1: 4-(N,N-dimethlyamino)pyridine 2: lithium triethylborohydride / toluene / -70 - -60 °C 3: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 4: water; lithium hydroxide hydrate / ethanol 5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 6: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 22, # 4 p. 1383 - 1393
反应条件
1: water; lithium hydroxide hydrate / ethanol 2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 3: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 16 h / 20 °C 2.2: pH 3 View Scheme
参考文献
BRISTOL-MYERS SQUIBB COMPANY; LOPEZ, Omar D.; ST. LAURENT, Denis R.; GOODRICH, Jason; ROMINE, Jeffrey Lee; SERRANO-WU, Michael; YANG, Fukang; KAKARLA, Ramesh; YANG, Xuejie; QIU, Yuping; SNYDER, Lawrence B.
Patent: WO2011/82077 A1, 2011 ;
反应条件
1: isopropyl alcohol / 60 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
反应条件
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
View Scheme
参考文献
Dong, Jizhe; Gong, Yanchun; Liu, Jun; Chen, Xiangfeng; Wen, Xiaoan; Sun, Hongbin
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1383 - 1393
