3: H2 / Pd/C 4: 85 percent / H2 / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr 5: dimethylformamide / 120 °C 6: 1.) MeNH2, 2.) HCl 8: H2 / Pd/C View Scheme

2: 85 percent / H2 / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr 3: dimethylformamide / 120 °C 4: 1.) MeNH2, 2.) HCl 6: H2 / Pd/C View Scheme

1: 85 percent / H2 / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr 2: dimethylformamide / 120 °C 3: 1.) MeNH2, 2.) HCl 5: H2 / Pd/C View Scheme

1: H2 / Pd/C 2: 85 percent / H2 / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr 3: dimethylformamide / 120 °C 4: 1.) MeNH2, 2.) HCl 6: H2 / Pd/C View Scheme

sodium hydroxide in chloroform; water T=30 - 35°C; pH=11 - 11.5; 0.166667 h; Product distribution / selectivity;

1: (COCl)2 2: 2.) H3O(+) / 1.) 90 deg C 4: NaBH4 6: p-TsOH, EtOH 7: t-BuOK 8: dimethylformamide / 120 °C 9: 1.) MeNH2, 2.) HCl 11: H2 / Pd/C View Scheme

1: 1.) carbonyldiimidazole 2: NaBH4 / ethanol / 1 h / -15 - -10 °C 3: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 4: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 5: (COCl)2, DMF / toluene / 1 h 6: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 7: aq. AcOH, conc. HCl / 3 h / Ambient temperature 8: 100 percent / KOH / methanol / 3 h / Ambient temperature 9: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 10: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 11: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 12: H2 / 10percent Pd/C / ethanol / 16 h 13: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 1.) carbonyldiimidazole 2: NaBH4 / ethanol / 1 h / -15 - -10 °C 3: 89 percent / TsOH*H2O / 5 h / 60 °C 4: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 5: (COCl)2, DMF / toluene / 1 h 6: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 7: aq. AcOH, conc. HCl / 3 h / Ambient temperature 8: 92 percent / KOH / methanol / 3 h / Ambient temperature 9: 86 percent / propan-2-ol / 6 h / 80 °C 10: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 11: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 12: H2 / 10percent Pd/C / ethanol / 16 h 13: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 2.) Bu4NF / 1.) THF 2: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature 3: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature 4: 96 percent / acetonitrile / 20 h / Heating 5: NaBH4 / methanol / 1 h / -10 °C 6: HgCl2 / acetonitrile; H2O / 0.25 h 7: NaCNBH3, 1 M HCl, 3-Angstroem molecular sieves / methanol / 112 h / Ambient temperature 8: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 9: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 10: H2 / 10percent Pd/C / ethanol / 16 h 11: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature 2: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature 3: 96 percent / acetonitrile / 20 h / Heating 4: NaBH4 / methanol / 1 h / -10 °C 5: HgCl2 / acetonitrile; H2O / 0.25 h 6: NaCNBH3, 1 M HCl, 3-Angstroem molecular sieves / methanol / 112 h / Ambient temperature 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