water; trifluoroacetic acid T=50°C; 3 h;

ammonia T=25°C; 18 h;

boron trichloride in dichloromethane T=-78 - 20°C; debenzylation; 0.583333 h;

1: 77 percent / H2 / [Rh(COD)dppb]BF4 / dimethylformamide / 18.5 h / 4137.29 Torr 2: LDA / tetrahydrofuran; hexane / 0.25 h / 0 °C 3: 55.4 mg / DIBAL / tetrahydrofuran / -78 - 0 °C 4: 87 percent / pyridine / CH2Cl2 / 0.33 h 5: 65 percent / Pd(PPh3)4 / dimethylformamide / 1.5 h / 10 °C 6: BCl3 / CH2Cl2 / 0.58 h / -78 - 20 °C View Scheme

1: 96 percent / Li2CO3 / methanol / 2.5 h 2: 77 percent / H2 / [Rh(COD)dppb]BF4 / dimethylformamide / 18.5 h / 4137.29 Torr 3: LDA / tetrahydrofuran; hexane / 0.25 h / 0 °C 4: 55.4 mg / DIBAL / tetrahydrofuran / -78 - 0 °C 5: 87 percent / pyridine / CH2Cl2 / 0.33 h 6: 65 percent / Pd(PPh3)4 / dimethylformamide / 1.5 h / 10 °C 7: BCl3 / CH2Cl2 / 0.58 h / -78 - 20 °C View Scheme

in ammonia

1: 93.4 percent / pyridine / 14 h / 0 - 20 °C 2: 93.3 percent / conc. HCl / methanol / 2.5 h / 20 °C 3: pyridinium p-toluene-sulfonate / 2 h / 20 °C 4: Ac2O / 6 h / 120 - 130 °C 5: 93.4 percent / 2 N NaOH / methanol / 1.5 h / 20 °C 6: 34.6 percent / diethyl azodicarboxylate; triphenylphosphine / dioxane / 10 h / 20 °C 7: 82.5 percent / NH3 / methanol / 20 h / 80 - 90 °C 8: 86 percent / aq. CF3CO2H / 3 h / 50 °C View Scheme

1: pyridinium p-toluene-sulfonate / 2 h / 20 °C 2: Ac2O / 6 h / 120 - 130 °C 3: 93.4 percent / 2 N NaOH / methanol / 1.5 h / 20 °C 4: 34.6 percent / diethyl azodicarboxylate; triphenylphosphine / dioxane / 10 h / 20 °C 5: 82.5 percent / NH3 / methanol / 20 h / 80 - 90 °C 6: 86 percent / aq. CF3CO2H / 3 h / 50 °C View Scheme

1: 93.3 percent / conc. HCl / methanol / 2.5 h / 20 °C 2: pyridinium p-toluene-sulfonate / 2 h / 20 °C 3: Ac2O / 6 h / 120 - 130 °C 4: 93.4 percent / 2 N NaOH / methanol / 1.5 h / 20 °C 5: 34.6 percent / diethyl azodicarboxylate; triphenylphosphine / dioxane / 10 h / 20 °C 6: 82.5 percent / NH3 / methanol / 20 h / 80 - 90 °C 7: 86 percent / aq. CF3CO2H / 3 h / 50 °C View Scheme

1: 34.6 percent / diethyl azodicarboxylate; triphenylphosphine / dioxane / 10 h / 20 °C 2: 82.5 percent / NH3 / methanol / 20 h / 80 - 90 °C 3: 86 percent / aq. CF3CO2H / 3 h / 50 °C View Scheme