1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C 2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature 3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating 5: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating 6: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h 8: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min 9: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr 10: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 11: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 12: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 13: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 14: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 15: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 16: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 17: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 18.1 g / 5percent NaOH aq. / methanol; CH2Cl2 / 1 h / Ambient temperature2: 21.7 g / pyridine / 1 h / Ambient temperature  

With  pyridine 1 h;  Ambient temperature;   

Multi-step reaction with 5 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating5: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating  

Multi-step reaction with 4 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating  

Multi-step reaction with 8 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating5: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating6: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h8: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min  

Multi-step reaction with 14 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature4: 14.0 g / p-toluenesulfonic acid / 2 h / Heating5: 12.7 g / 5percent NaOH, MeOH / 1 h / Heating6: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h8: 1.) K2CO3 / 1.) DMF, 100 deg C, 2 h, 2.) 50 deg C, 20 min9: 93 percent / H2 / 5percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr10: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature11: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C12: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature13: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature14: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h  

With  lithium bromide in  N,N-dimethyl-formamide T=140°C; 1 h;   

Multi-step reaction with 3 steps 1: 80 percent / LiBr / dimethylformamide / 1 h / 140 °C2: 14.8 g / OsO4, N-methylmorpholine N-oxide, H2O / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Ambient temperature3: 88 percent / p-toluenesulfonic acid / 2 h / Ambient temperature