(3R)-3-氨基-3-苯基丙酸叔丁酯合成路线 （共 25 条）
反应条件
1: 1.) (R)-binaphthol, B(OMe)3, 4 Angstroem molecular sieves / 1.) CH2Cl2, toluene, 0 deg C, 10 min, 2.) CH2Cl2, toluene, -78 deg C, 20 h
2: 83 percent / H2 / 10percent Pd/C / methanol / 14 h / 760 Torr / Ambient temperature
View Scheme
参考文献
Ishihara, Kazuaki; Miyata, Mayumi; Hattoi, Kouji; Tada, Toshiji; Yamamoto, Hisashi
Journal of the American Chemical Society, 1994 , vol. 116, # 23 p. 10520 - 10524
反应条件
1: MgSO4 / benzene / Ambient temperature
2: 1.) (R)-binaphthol, B(OMe)3, 4 Angstroem molecular sieves / 1.) CH2Cl2, toluene, 0 deg C, 10 min, 2.) CH2Cl2, toluene, -78 deg C, 20 h
3: 83 percent / H2 / 10percent Pd/C / methanol / 14 h / 760 Torr / Ambient temperature
View Scheme
参考文献
Ishihara, Kazuaki; Miyata, Mayumi; Hattoi, Kouji; Tada, Toshiji; Yamamoto, Hisashi
Journal of the American Chemical Society, 1994 , vol. 116, # 23 p. 10520 - 10524
反应条件
hydroxylamine hydrochloride in tetrahydrofuran; water
T=20°C; 0.25 h;
参考文献
Sakai, Takeo; Doi, Hirohisa; Tomioka, Kiyoshi
Tetrahedron, 2006 , vol. 62, # 35 p. 8351 - 8359
反应条件
hydrogen; palladium dihydroxide in ethanol
P=2850.23 Torr; 72 h; Title compound not separated from byproducts;
参考文献
Sergeyev, Sergey A.; Hesse, Manfred
Helvetica Chimica Acta, 2002 , vol. 85, # 1 p. 161 - 167
反应条件
1: With N-dibutylamino-DBU in toluene
T=20°C; 24 h;
2: With hydroxylamine hydrochloride in tetrahydrofuran; water
T=20°C; 0.25 h;
参考文献
Sakai, Takeo; Kawamoto, Yoshito; Tomioka, Kiyoshi
Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4706 - 4709
反应条件
1: With N-iodo-succinimide in dichloromethane
T=20°C; Inert atmosphere;
2: With water; sodium hydrogencarbonate; sodium thiosulfate in dichloromethane
T=20°C; Inert atmosphere;
参考文献
Node, Manabu; Hashimoto, Daisuke; Katoh, Takahiro; Ochi, Shunsuke; Ozeki, Minoru; Watanabe, Tsunefumi; Kajimoto, Tetsuya
Organic Letters, 2008 , vol. 10, # 13 p. 2653 - 2656
反应条件
ammonium cerium(IV) nitrate in acetonitrile
T=20°C; 16 h;
参考文献
Bull, Steven D.; Davies, Stephen G.; Kelly, Peter M.; Gianotti, Massimo; Smith, Andrew D.
Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 23 p. 3106 - 3111
反应条件
methanesulfonic acid in dichloromethane
T=20°C; Elimination; Product distribution; Further Variations:Reagents;
参考文献
Lin; Lanza T.; De Laszlo; Truong; Kamenecka; Hagmann
Tetrahedron Letters, 2000 , vol. 41, # 36 p. 7013 - 7016
反应条件
1: 73 percent / Et3N / 12 h / 90 °C
2: BuLi / tetrahydrofuran; hexane / 1 h
3: H2 / Pd(OH)2/C / ethanol / 72 h / 2850.23 Torr
View Scheme
参考文献
Sergeyev, Sergey A.; Hesse, Manfred
Helvetica Chimica Acta, 2002 , vol. 85, # 1 p. 161 - 167
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.2: 96 percent / tetrahydrofuran; hexane / -78 - 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 96 percent / tetrahydrofuran; hexane / 3 h / -78 °C
3.1: 89 percent / H2; acetic acid / Pd(OH)2/C / methanol; H2O / 24 h / 20 °C / 760.05 Torr
View Scheme
参考文献
Davies, Stephen G.; Mulvaney, Andrew W.; Russell, Angela J.; Smith, Andrew D.
Tetrahedron Asymmetry, 2007 , vol. 18, # 13 p. 1554 - 1566
