methanol; boron trifluoride in dichloromethane 4 h; Ambient temperature;

1: pyridine 2: NaH 3: TsOH / methanol; CH2Cl2 View Scheme

1: 92 percent / NaH / tetrahydrofuran / Ambient temperature 2: 76 percent / boron trifluoride/methanol / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 95 percent / pyridine; dimethylformamide / 2 h 2: 63 percent / pyridine / 10 h / 50 °C 3: 92 percent / NaH / tetrahydrofuran / Ambient temperature 4: 76 percent / boron trifluoride/methanol / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 2-bromoethyl phosphorodichloridate; (+/-)-3-octadecanamido-2-methoxy-1-propanol Alkylation; 2: trimethylamine With water in chloroform; N,N-dimethyl-formamide; isopropyl alcohol Amination;

triethylamine 1.) benzene, RT, 4 h, 2.) CH3CN, 65 deg C; Yield given. Multistep reaction;