1: NaCNBH3, 1 M HCl, 3-Angstroem molecular sieves / methanol / 112 h / Ambient temperature 2: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 3: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 16 h 5: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 2.) 10percent H2SO4 / 1.) THF, r.t., 2.) 70percent aq. MeOH, reflux, 4 h 2: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h / 2585.7 Torr / Ambient temperature 3: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 16 h 5: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 92 percent / KOH / methanol / 3 h / Ambient temperature 2: 86 percent / propan-2-ol / 6 h / 80 °C 3: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 4: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 16 h 6: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 2: aq. AcOH, conc. HCl / 3 h / Ambient temperature 3: 100 percent / KOH / methanol / 3 h / Ambient temperature 4: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 5: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 6: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 7: H2 / 10percent Pd/C / ethanol / 16 h 8: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: (COCl)2, DMF / toluene / 1 h 2: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 3: aq. AcOH, conc. HCl / 3 h / Ambient temperature 4: 100 percent / KOH / methanol / 3 h / Ambient temperature 5: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 6: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 7: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 8: H2 / 10percent Pd/C / ethanol / 16 h 9: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 89 percent / TsOH*H2O / 5 h / 60 °C 3: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 92 percent / KOH / methanol / 3 h / Ambient temperature 8: 86 percent / propan-2-ol / 6 h / 80 °C 9: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 10: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 11: H2 / 10percent Pd/C / ethanol / 16 h 12: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: (COCl)2, DMF / toluene / 1 h 2: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 3: aq. AcOH, conc. HCl / 3 h / Ambient temperature 4: 92 percent / KOH / methanol / 3 h / Ambient temperature 5: 86 percent / propan-2-ol / 6 h / 80 °C 6: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 7: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 8: H2 / 10percent Pd/C / ethanol / 16 h 9: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 2: aq. AcOH, conc. HCl / 3 h / Ambient temperature 3: 92 percent / KOH / methanol / 3 h / Ambient temperature 4: 86 percent / propan-2-ol / 6 h / 80 °C 5: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 6: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 7: H2 / 10percent Pd/C / ethanol / 16 h 8: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 2: (COCl)2, DMF / toluene / 1 h 3: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 4: aq. AcOH, conc. HCl / 3 h / Ambient temperature 5: 100 percent / KOH / methanol / 3 h / Ambient temperature 6: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 7: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 8: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 9: H2 / 10percent Pd/C / ethanol / 16 h 10: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 69 percent / t-BuOK / dimethylformamide / 1 h / 20 °C 2: 80 percent / dimethylformamide / 8.5 h / 120 °C 3: 1.) 33percent MeNH2, 2.) 4 M HCl / 1.) EtOH, r.t., 1 h, 2.) EtOH, EtOAc, r.t., overnight 4: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 16 h 6: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme