Multi-step reaction with 10 steps
1: 1.) 55percent NaH (in mineral oil), 2.) acetic acid / 1.) DMSO, 1.5 h, room temperature, 2.) DMSO, 20 h, room temperature
2: 45 percent / DCC / CH2Cl2 / 0.5 h / Ambient temperature
3: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating
4: 98 percent / silicagel powder, NaBH4 / methanol / 0.25 h
5: 79 percent / H2O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating
6: 86 percent / Ag2O / dimethylformamide / 4 h / Ambient temperature
7: 88 percent / LiAlH4 / tetrahydrofuran / 5 °C
8: 48.3 percent / H2 / 10percent Pd/C / ethanol / 5 h
9: 97 percent / triethylamine / tetrahydrofuran / 0.25 h / Ambient temperature
10: pyridine / Ambient temperature
With
sodium tetrahydroborate; lithium aluminium tetrahydride; water; hydrogen; silica gel; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.62.3950