tetrabutyl ammonium fluoride in tetrahydrofuran 0.5 h; Ambient temperature;

tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 0.0833333 h;

1: sodium methylate / methanol / 0.17 h / 20 °C 2: toluene-4-sulfonic acid / methanol / 3 h / 20 °C View Scheme

sodium methylate in methanol T=20°C; 0.166667 h;

1: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h 2: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature 3: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature 4: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 5: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 6: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme