methanesulfonic acid in ethanol T=35 - 40°C; Yield given;

1: 97 percent / K2CO3 / H2O / 58 h / 22 °C 2: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C 3: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr 4: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C 5: NaBH4 / toluene / 0.5 h / -2 °C 6: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 7: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 8: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 9: MsOH / ethanol / 7.5 h / 35 - 40 °C 10: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 11: MsOH / ethanol / 35 - 40 °C View Scheme

1: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C 2: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr 3: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C 4: NaBH4 / toluene / 0.5 h / -2 °C 5: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 6: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 7: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 8: MsOH / ethanol / 7.5 h / 35 - 40 °C 9: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 10: MsOH / ethanol / 35 - 40 °C View Scheme

1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C 2: NaBH4 / toluene / 0.5 h / -2 °C 3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 6: MsOH / ethanol / 7.5 h / 35 - 40 °C 7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 8: MsOH / ethanol / 35 - 40 °C View Scheme

1: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr 2: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C 3: NaBH4 / toluene / 0.5 h / -2 °C 4: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 5: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 6: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 7: MsOH / ethanol / 7.5 h / 35 - 40 °C 8: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 9: MsOH / ethanol / 35 - 40 °C View Scheme

1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C 2: NaBH4 / toluene / 0.5 h / -2 °C 3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 6: MsOH / ethanol / 7.5 h / 35 - 40 °C 7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 8: MsOH / ethanol / 35 - 40 °C View Scheme

1: NaBH4 / toluene / 0.5 h / -2 °C 2: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 3: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 4: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 5: MsOH / ethanol / 7.5 h / 35 - 40 °C 6: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 7: MsOH / ethanol / 35 - 40 °C View Scheme

1: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C 2: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 3: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 4: MsOH / ethanol / 7.5 h / 35 - 40 °C 5: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 6: MsOH / ethanol / 35 - 40 °C View Scheme

1: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr 2: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 3: MsOH / ethanol / 7.5 h / 35 - 40 °C 4: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 5: MsOH / ethanol / 35 - 40 °C View Scheme

1: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature 2: MsOH / ethanol / 7.5 h / 35 - 40 °C 3: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature 4: MsOH / ethanol / 35 - 40 °C View Scheme