1: 89 percent / NaNO2; AcOH / H2O / 2 h / 0 - 20 °C 2: 82 percent / diphenyl phosphoryl azide; DEAD; PPh3 / tetrahydrofuran / 12 h / 0 - 20 °C 3: 97 percent / H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr 4: 100 percent / DMAP; pyridine 5: HNO3; H2SO4 / 1.5 h / -20 - 20 °C 6: aq. HCl / 90 °C View Scheme

1: 98 percent / MgBr2*Et2O / diethyl ether / 2 h / -60 °C 2: 99 percent / NaN3 / dimethylformamide / 48 h / 65 °C 3: 1.) DMAP, 2.) H2 / 2.) Pd/C / 1.) CH2Cl2, rt, 1 h, 2.) MeOH, 25 deg C, 4 h View Scheme

1: 89 percent / NaNO2; AcOH / H2O / 2 h / 0 - 20 °C 2: 82 percent / diphenyl phosphoryl azide; DEAD; PPh3 / tetrahydrofuran / 12 h / 0 - 20 °C 3: 97 percent / H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr 4: 100 percent / DMAP; pyridine 5: HNO3; H2SO4 / 1.5 h / -20 - 20 °C 6: aq. HCl / 90 °C View Scheme

1: 89 percent / NaNO2; AcOH / H2O / 2 h / 0 - 20 °C 2: 82 percent / diphenyl phosphoryl azide; DEAD; PPh3 / tetrahydrofuran / 12 h / 0 - 20 °C 3: 97 percent / H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr 4: 100 percent / DMAP; pyridine 5: HNO3; H2SO4 / 1.5 h / -20 - 20 °C 6: aq. HCl / 90 °C 7: 80 percent / 1 h / 90 °C View Scheme

1: 89 percent / NaNO2; AcOH / H2O / 2 h / 0 - 20 °C 2: 82 percent / diphenyl phosphoryl azide; DEAD; PPh3 / tetrahydrofuran / 12 h / 0 - 20 °C 3: 97 percent / H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr View Scheme

1: NaOH / tetrahydrofuran; H2O / 0.33 h / Ambient temperature 2: 5.55 g / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 0.17 h / Ambient temperature 3: 76 percent / hexamethylphosphoramide, TiBr4 / CH2Cl2 / 18 h / 0 °C 4: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C 5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature View Scheme

1: 90 percent / HNEt2*HBr, Et2AlCl / CH2Cl2 / 2.5 h / -15 °C 2: 80 percent / NaN3 / dimethylformamide / 40 h / 65 - 75 °C 3: 93 percent / DMAP / CH2Cl2 / 1 h / 23 °C 4: 74 percent / H2 / 10percent Pd-C / methanol / 4 h / 2585.7 Torr 5: 80 percent / aq. K2CO3 / methanol / 12 h / 23 °C View Scheme

1: NaOH / tetrahydrofuran; H2O / 0.33 h / Ambient temperature 2: 5.55 g / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 0.17 h / Ambient temperature 3: 76 percent / hexamethylphosphoramide, TiBr4 / CH2Cl2 / 18 h / 0 °C 4: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C 5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature 6: 79 percent / acetic acid, zinc / methanol / 0.67 h / 60 °C View Scheme

1: 89 percent / NaNO2; AcOH / H2O / 2 h / 0 - 20 °C 2: 82 percent / diphenyl phosphoryl azide; DEAD; PPh3 / tetrahydrofuran / 12 h / 0 - 20 °C 3: 97 percent / H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr 4: 100 percent / DMAP; pyridine 5: HNO3; H2SO4 / 1.5 h / -20 - 20 °C 6: aq. HCl / 90 °C View Scheme