1: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 2: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

Multi-step reaction with 14 steps 1: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature2: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature3: 14.0 g / p-toluenesulfonic acid / 2 h / Heating4: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h7: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min8: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature9: 71 percent / DBU / benzene / 0.5 h / Heating10: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr11: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature12: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C13: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature14: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 16 steps 1: 21.7 g / pyridine / 1 h / Ambient temperature2: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C3: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature4: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature5: 14.0 g / p-toluenesulfonic acid / 2 h / Heating6: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating7: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature8: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h9: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min10: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature11: 71 percent / DBU / benzene / 0.5 h / Heating12: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr13: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature14: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C15: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature16: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 10 steps 1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h3: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min4: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature5: 71 percent / DBU / benzene / 0.5 h / Heating6: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr7: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature8: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C9: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature10: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 9 steps 1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h2: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min3: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature4: 71 percent / DBU / benzene / 0.5 h / Heating5: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr6: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature7: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C8: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature9: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 17 steps 1: 18.1 g / 5percent NaOH aq. / methanol; CH2Cl2 / 1 h / Ambient temperature2: 21.7 g / pyridine / 1 h / Ambient temperature3: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C4: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature5: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature6: 14.0 g / p-toluenesulfonic acid / 2 h / Heating7: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating8: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature9: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h10: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min11: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature12: 71 percent / DBU / benzene / 0.5 h / Heating13: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr14: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature15: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C16: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature17: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature  

Multi-step reaction with 12 steps 1: 14.0 g / p-toluenesulfonic acid / 2 h / Heating2: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h5: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min6: 93 percent / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / 1 h / Ambient temperature7: 71 percent / DBU / benzene / 0.5 h / Heating8: 92 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr9: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature10: 83 mg / triethylamine / CH2Cl2 / 0.17 h / 0 °C11: 65 mg / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature12: 82 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature