hydrogen; palladium on activated charcoal in methanol

1: (i), (ii) /BRN= 878307/, Et3N 2: H2 / Pd-C / methanol View Scheme

trifluoroacetic acid in dichloromethane 0.5 h; Ambient temperature;

1: 98 percent / TEA, 4-DMAP / dimethylformamide / 3 h / Ambient temperature 2: 90 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 1 h / Ambient temperature 3: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h 4: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature 5: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature 6: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 7: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 92 percent / LiBH4 / tetrahydrofuran / 15 h / 5 °C 2: 98 percent / TEA, 4-DMAP / dimethylformamide / 3 h / Ambient temperature 3: 90 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 1 h / Ambient temperature 4: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h 5: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature 6: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature 7: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 8: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

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

1: 90 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 1 h / Ambient temperature 2: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h 3: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature 4: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature 5: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 6: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 2: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 3: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH2Cl2, 3 h, room temperature 2: 69 percent / TEA, benzyl alcohol / 24 h / 105 °C 3: hydrogen / 10percent Pd/C / ethanol / Ambient temperature 4: 90 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

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