1: With hydrogen; palladium on activated charcoal in methanol P=3750.3 Torr; 2: With (+)-di-p-toluoyl-D-tartaric acid in methanol T=22 - 25°C; 5 h; 3: With sodium carbonate in methyl acetate T=20 - 25°C; 0.5 h;

ammonium formate; Pd/C (10percent) in methanol; water; acetic acid T=38 - 42°C;

1.1: H2SO4; aq. HNO3 / acetic acid; acetic anhydride / 2.5 h / -5 - 5 °C 2.1: Na2CO3 / methyl acetate; H2O / 20 - 25 °C 2.2: 97.8 percent / methyl acetate; H2O / 1 h / 20 - 25 °C 3.1: H2 / Pd/C (5 percent) / methanol / 3750.3 Torr 3.2: (+)-di-p-toluoyl-D-tartaric acid / methanol / 5 h / 22 - 25 °C 3.3: 6.95 g / aq. Na2CO3 / methyl acetate / 0.5 h / 20 - 25 °C View Scheme

1.1: Br2 / H2O / 58 - 62 °C 1.2: (1R)-(-)-10-camphorsulfonic acid / methanol; isopropyl acetate / 60 - 65 °C 1.3: aq. NaOH; NaCl / isopropyl acetate / 20 - 25 °C 2.1: 86 percent / NaHCO3 / isopropyl acetate; H2O / 1 h / 0 - 5 °C 3.1: (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOCH3 / tris(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 78 - 82 °C 4.1: 45.36 g / aq. HCl / toluene / 1.5 h / 60 - 65 °C View Scheme

1: 86 percent / NaHCO3 / isopropyl acetate; H2O / 1 h / 0 - 5 °C 2: (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOCH3 / tris(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 78 - 82 °C 3: 45.36 g / aq. HCl / toluene / 1.5 h / 60 - 65 °C View Scheme

1: (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOCH3 / tris(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 78 - 82 °C 2: 45.36 g / aq. HCl / toluene / 1.5 h / 60 - 65 °C View Scheme

1.1: nitric acid; trifluoroacetic acid; trifluoroacetic anhydride / CH2Cl2 / -35 - -30 °C 2.1: NaOH; methanol / 23 °C 3.1: acetic acid; perchloric acid; hydrogen / Pd/C / 15.5 h / 2172.08 - 2585.81 Torr 3.2: NaHCO3 / H2O; CH2Cl2 / 23 °C / pH 8.0 View Scheme

1.1: aq. sodium hydroxide; sodium carbonate / 0 - 23 °C 2.1: phosphorus pentachloride / CH2Cl2 / -10 - 20 °C 3.1: aluminum chloride / CH2Cl2 / 22 - 28 °C 3.2: aq. HCl / CH2Cl2 / -5 - 1 °C 4.1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 °C 5.1: pyridine / CH2Cl2 / -5 - 0 °C 6.1: nitric acid; trifluoroacetic acid; trifluoroacetic anhydride / CH2Cl2 / -35 - -30 °C 7.1: NaOH; methanol / 23 °C 8.1: acetic acid; perchloric acid; hydrogen / Pd/C / 15.5 h / 2172.08 - 2585.81 Torr 8.2: NaHCO3 / H2O; CH2Cl2 / 23 °C / pH 8.0 View Scheme

1.1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 °C 2.1: pyridine / CH2Cl2 / -5 - 0 °C 3.1: nitric acid; trifluoroacetic acid; trifluoroacetic anhydride / CH2Cl2 / -35 - -30 °C 4.1: NaOH; methanol / 23 °C 5.1: acetic acid; perchloric acid; hydrogen / Pd/C / 15.5 h / 2172.08 - 2585.81 Torr 5.2: NaHCO3 / H2O; CH2Cl2 / 23 °C / pH 8.0 View Scheme

1.1: phosphorus pentachloride / CH2Cl2 / -10 - 20 °C 2.1: aluminum chloride / CH2Cl2 / 22 - 28 °C 2.2: aq. HCl / CH2Cl2 / -5 - 1 °C 3.1: Red-Al; sodium bis(2-methoxyethoxy)aluminum hydride / toluene; tetrahydrofuran / -10 - 0 °C 4.1: pyridine / CH2Cl2 / -5 - 0 °C 5.1: nitric acid; trifluoroacetic acid; trifluoroacetic anhydride / CH2Cl2 / -35 - -30 °C 6.1: NaOH; methanol / 23 °C 7.1: acetic acid; perchloric acid; hydrogen / Pd/C / 15.5 h / 2172.08 - 2585.81 Torr 7.2: NaHCO3 / H2O; CH2Cl2 / 23 °C / pH 8.0 View Scheme