1: 96 percent / 2,6-di-t-butyl-4-methylpyridine / CH2Cl2 2: 1.) CsOAc ; 2.) LiAlH4 / 1.) DMF,DMSO ; 2.) Et2O 3: 1.) POCl3,Et3N ; 2.) pyridine / 1.) CHCl3 ; 2.) rt 4: H2 / Pd(OH)2/C / methanol; H2O / 24 h 5: DMAP / CHCl3 View Scheme

1: 96 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 4 h / -78 - 25 °C 2: dimethylsulfoxide; dimethylformamide / 36 h / Ambient temperature 3: LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h 4: POCl3, Et3N / CHCl3 / 0.5 h / Ambient temperature 5: 1.) pyridine, 2.) water / 1.) CHCl3, RT, 16 h, 2.) 30 min 6: 100 percent / H2 / 20percent Pd(OH)2/C / methanol; H2O / 24 h 7: 98 percent / 4-(dimethylamino)pyridine / CHCl3 / 24 h View Scheme

1: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 16 h / Heating 2: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature 3: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 4: acetonitrile / 36 h / 65 - 70 °C View Scheme

1: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 16 h / Heating 2: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature View Scheme

Multi-step reaction with 4 steps 1.1: 95 percent / CF3SO3H / dioxane / 0.67 h2.1: dimethylformamide; dimethylsulfoxide / 60 °C3.1: 1.24 g / LiAlH4 / diethyl ether / 3.5 h / 0 - 20 °C4.1: POCl3; Et3N / CH2Cl2 / 0.5 h4.2: 81 percent / pyridine / CH2Cl2 / 20 °C  

Multi-step reaction with 3 steps 1: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 16 h / Heating2: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature3: 100 percent / triethylamine / benzene / 2 h / Ambient temperature