(3aR,4S,5R,6aS)-(-)-六氢-4-(羟甲基)-2-氧代-2H-环戊并[b]呋喃-5-基 1,1'-联苯-4-甲酸酯合成路线 （共 14 条）
反应条件
1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature
2: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature
View Scheme
参考文献
Terinek, Miroslav; Kozmik, Vaclav; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1997 , vol. 62, # 8 p. 1325 - 1341
反应条件
1: trichloroisocyanuric acid; potassium acetate; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / dichloromethane / 1.09 h / -5 - 17 °C
2: triethylamine; lithium chloride / tetrahydrofuran / 15.5 h / -10 - -5 °C
View Scheme
参考文献
LUPIN LIMITED; KAMMILI, Venkata, Rambabu; SMART, Anurag, Anil; SIYAN, Rajinder, Singh; BHISE, Nandu, Baban; SINGH, Girij, Pal
Patent: WO2013/164729 A1, 2013 ;
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h
2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h
3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
4: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
5: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature
6: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h
2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h
View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
