3-chloro-benzenecarboperoxoic acid in dichloromethane Ambient temperature;

1: 99 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 96 percent / MnO2 / CH2Cl2 / 6 h / Ambient temperature 3: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 4: 99 percent / ethyl formate / 20 h / Ambient temperature 5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 7: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 8: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 20 h / Ambient temperature 3: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 4: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 5: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 6: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 2: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 3: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 2: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 3: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 4: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 80 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 2: 99 percent / ethyl formate / 12 h / Ambient temperature 3: 75 percent / methanesulfonic acid / 3.5 h / 70 °C / other reagent: polyphosphoric acid 4: 72 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 12 h / Ambient temperature; other reactant: 9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline, other reagent: benzoquinone, other reaction time 5: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 72 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 12 h / Ambient temperature; other reactant: 9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline, other reagent: benzoquinone, other reaction time 2: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 75 percent / methanesulfonic acid / 3.5 h / 70 °C / other reagent: polyphosphoric acid 2: 72 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 12 h / Ambient temperature; other reactant: 9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline, other reagent: benzoquinone, other reaction time 3: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 1.) LiAlH4, 2.) MnO2 / 1.) THF, RT, 2.) CH2Cl2, RT 2: 1.) NaBH3CN / 1.) MeOH, RT, 2.) RT 3: 67 percent / PPA / 60 °C 4: 69 percent / TsOH, chloranil / benzene / Ambient temperature 5: 81 percent / m-CPBA / CH2Cl2 / Ambient temperature View Scheme

1: 61 percent / triethylamine / acetonitrile / 5 h / 70 °C 2: 97 percent / KOH / acetonitrile; H2O / 14 h / Ambient temperature 3: 2.) SiO2 / 1.) THF, hexane, -50 deg C, 30 min, 2.) 1 week; other reagent: H(1+) View Scheme