1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 2: 90 percent / hydrogen / 10 percent Pd/C / methanol; ethyl acetate / 3 h / 1551.44 Torr 3: 79 percent / bistrimethylsilylurea; BH3-Me2S / CH2Cl2 / 5 h / -20 - -15 °C View Scheme

1: (nBu)3N / heptane; toluene / 80 - 90 °C 2: LiOH*H2O / methanol / 2 h 3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 5: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 6: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme

1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 3: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 4: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme

1: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 2: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 3: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme

1: LiOH*H2O / methanol / 2 h 2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 4: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 5: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme

1: With sulfuric acid; sodium nitrite in water; N,N-dimethyl-formamide T=0°C; 1.5 h; 2: With urea in water; N,N-dimethyl-formamide T=20 - 90°C; 0.416667 h; 3: With sodium hydrogencarbonate in water; N,N-dimethyl-formamide Product distribution / selectivity;

1: With dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole in dichloromethane T=0 - 5°C; 0.25 h; 2: With water; dihydrogen peroxide in dichloromethane T=0 - 20°C; 0.5 h; Product distribution / selectivity;

1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / |Molecular sieve 1.2: 5 h / 20 °C 2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C 3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h 4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C 5.1: toluene / 72 h / |Reflux 6.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C 7.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C 7.2: 0.25 h / 20 °C 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 18 h 9.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C 10.1: 1,1-dimethylethylmagnesium chloride / diethyl ether / 2 h / 0 °C 11.1: hydrogen; palladium 10 on activated carbon / ethyl acetate; methanol / 18 h / 750.08 Torr View Scheme

1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h 2: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C 3: toluene / 72 h / |Reflux 4: lithium hydroxide hydrate / tetrahydrofuran; water / 18 h 5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C 6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C 7: Burgess Reagent / toluene / 18 h / 90 °C 8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr 9: 1,1-dimethylethylmagnesium chloride / diethyl ether / 2 h / 0 °C 10: hydrogen; palladium 10 on activated carbon / ethyl acetate; methanol / 18 h / 750.08 Torr View Scheme

1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / |Reflux 2: methanesulfonic acid / acetone / 2 h / 20 °C 3: toluene / 72 h / |Reflux 4: lithium hydroxide hydrate / tetrahydrofuran; water / 18 h 5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C 6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C 7: Burgess Reagent / toluene / 18 h / 90 °C 8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr 9: 1,1-dimethylethylmagnesium chloride / diethyl ether / 2 h / 0 °C 10: hydrogen; palladium 10 on activated carbon / ethyl acetate; methanol / 18 h / 750.08 Torr View Scheme