4-(N,N-dimethlyamino)pyridine in chloroform 24 h;

1.1: NaH / tetrahydrofuran / 1 h / 80 °C 1.2: tetrahydrofuran; dimethylformamide / 80 °C 2.1: 2.39 g / pyridine / petroleum ether / 16 h / 80 °C 3.1: H2 / Pd/C / ethyl acetate / 1.5 h 4.1: POCl3; Et3N / CH2Cl2 / 0.5 h / 20 °C 4.2: 159 mg / pyridine / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 2.39 g / pyridine / petroleum ether / 16 h / 80 °C 2.1: H2 / Pd/C / ethyl acetate / 1.5 h 3.1: POCl3; Et3N / CH2Cl2 / 0.5 h / 20 °C 3.2: 159 mg / pyridine / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: H2 / Pd/C / ethyl acetate / 1.5 h 2.1: POCl3; Et3N / CH2Cl2 / 0.5 h / 20 °C 2.2: 159 mg / pyridine / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 2.39 g / pyridine / petroleum ether / 16 h / 80 °C 2.1: H2 / Pd/C / ethyl acetate / 1.5 h 3.1: POCl3; Et3N / CH2Cl2 / 0.5 h / 20 °C 3.2: 159 mg / pyridine / CH2Cl2 / 16 h / 20 °C View Scheme

1: 2-O-hexadecanoyl-1-O-hexadecyl-sn-glycerol With triethylamine; trichlorophosphate in dichloromethane T=20°C; 0.5 h; 2: choline p-toluenesulfonate With pyridine in dichloromethane T=20°C; 16 h;

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

1: 100 percent / H2 / 20percent Pd(OH)2/C / methanol; H2O / 24 h 2: 98 percent / 4-(dimethylamino)pyridine / CHCl3 / 24 h View Scheme