N-Boc-L-苯丙氨醛合成路线 （共 60 条）
反应条件
1: 39 percent / BnEt3N(1+)*Cl(1-) / H2O; CH2Cl2 / 0 °C 2: 53 percent / H2, AcOH / Raney Ni / methanol / 750.06 Torr / Ambient temperature 3: NaBH3CN, TsOH / 1,2-dimethoxy-ethane / Ambient temperature 4: 1.) aq. borax; 2.) MTBD 5: 60 percent / DIBAH / 2.5 h / 0 °C View Scheme
参考文献
Faessler, Alex; Bold, Guido; Steiner, Heinz
Tetrahedron Letters, 1998 , vol. 39, # 27 p. 4925 - 4928
反应条件
1: 1.) n-BuLi / 1.) THF, hexane, -80 deg C, 1 h, 2.) a) -80 deg C, 1 h, b) room temp. 2: 1.) (cyclohexyl)2BH, 2.) 2 N NaOH, 30percent H2O2 / 1.) THF, 0 deg C, 1 h, 2.) MeOH, room temp., 1 h 3: 64 percent / 1,1'-carbonyldiimidazole (CDI) / tetrahydrofuran / 3 h 4: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 72 h / Ambient temperature 5: 1.1 g / 1 N NaOH / methanol / 2 h / Ambient temperature 6: HOBT/DCC, Et3N / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) room temp. 7: H2 / Raney Ni / methanol / 24 °C / 2585.7 Torr View Scheme
参考文献
Kaltenbronn; Hudspeth; Lunney; Michniewicz; Nicolaides; Repine; Roark; Stier; Tinney; Woo; Essenburg
Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 838 - 845
反应条件
TiCl3(DME)2; copper; zinc in ethylene glycol dimethyl ether
T=0°C; 1 h; Yield given;
参考文献
Kempf, Dale J.; Sowin, Thomas J.; Doherty, Elizabeth M.; Hannick, Steven M.; Codavoci, LynnMarie; et al.
Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5692 - 5700
反应条件
1: 2.) Bu4NF / 1.) THF
2: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature
3: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature
4: 96 percent / acetonitrile / 20 h / Heating
5: NaBH4 / methanol / 1 h / -10 °C
6: HgCl2 / acetonitrile; H2O / 0.25 h
7: NaCNBH3, 1 M HCl, 3-Angstroem molecular sieves / methanol / 112 h / Ambient temperature
8: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature
9: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature
View Scheme
参考文献
Parkes, Kevin E. B.; Bushnell, David J.; Crackett, Peter H.; Dunsdon, Stephen J.; Freeman, Andrew C.; et al.
Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3656 - 3664
反应条件
1: 35 percent / Et3N, LiClO4 / CH2Cl2 / 4 h / -78 °C
2: 81 percent / H2, Et3N / Pd/C / ethyl acetate / 15 h / 760 Torr
View Scheme
参考文献
Bandyopadhyay, Anupam; Malik, Ankita; Kumar, Mothukuri Ganesh; Gopi, Hosahudya N.
Organic Letters, 2014 , vol. 16, # 1 p. 294 - 297
反应条件
1: ethyl acetate With lithium diisopropyl amide in tetrahydrofuran; hexane; ethylbenzene
T=-78°C;
2: [(1S)-1-formyl-2-phenylethyl]-carbamic acid 1,1-dimethylethyl ester in tetrahydrofuran; hexane; ethylbenzene
T=-78 - 0°C;
参考文献
Gupta, Deepak; Yedidi, Ravikiran S.; Varghese, Sheeba; Kovari, Ladislau C.; Woster, Patrick M.
Journal of Medicinal Chemistry, 2010 , vol. 53, # 10 p. 4234 - 4247
反应条件
zinc dibromide; lithium diisopropyl amide in tetrahydrofuran
T=-78 - 20°C; Inert atmosphere; stereoselective reaction;
参考文献
Mohapatra, Debendra K.; Thirupathi, Barla; Das, Pragna P.; Yadav, Jhillu S.
Beilstein Journal of Organic Chemistry, 2011 , vol. 7, p. 34 - 39
反应条件
zinc in tetrahydrofuran
0.75 h; Heating;
参考文献
Camplo; Niddam; Barthelemy; Faury; Mourier; Simon; Charvet; Trabaud; Graciet; Chermann; Kraus
European Journal of Medicinal Chemistry, 1995 , vol. 30, # 10 p. 789 - 800
反应条件
1: benzene / Heating
2: aq. HCl / dioxane
View Scheme
参考文献
Hagihara, Masahiko; Anthony, Neville J.; Stout, Thomas J.; Clardy, Jon; Schreiber, Stuart L.
Journal of the American Chemical Society, 1992 , vol. 114, # l6 p. 6568 - 6570
反应条件
1: Methyltriphenylphosphonium bromide With potassium tert-butylate in tetrahydrofuran; toluene
T=25°C; 16 h;
2: [(1S)-1-formyl-2-phenylethyl]-carbamic acid 1,1-dimethylethyl ester in tetrahydrofuran; toluene
T=-78 - 25°C; 1.75 h;
参考文献
ABBOTT LABORATORIES
Patent: WO2005/61487 A1, 2005 ;
Location in patent: Page/Page column 114 ;
WO 2005/061487 A1
