hydrogen; palladium on activated charcoal in ethanol P=775.7 Torr; 0.25 h;

1: 61 percent / hexamethylenetetramine, glacial acetic acid, sulfuric acid / 18 h / 25 °C 2: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 3: 49 percent / trifluoroacetic acid / 0.25 h / Heating 4: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 5: hexane; methanol / 14 h / Heating 6: hydrochloric acid / ethanol 7: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: hexane; methanol / 14 h / Heating 2: hydrochloric acid / ethanol 3: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: hydrochloric acid / ethanol 2: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 80 percent / potassium carbonate, N, N-dimethylformamide / 1.5 h / Heating 2: 49 percent / trifluoroacetic acid / 0.25 h / Heating 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol 6: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 6: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 7: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 9: hexane; methanol / 14 h / Heating 10: hydrochloric acid / ethanol 11: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 82 percent / N,N-dimethylaniline / 2.5 h / 193 °C 2: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 3: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 4: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 5: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 6: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 7: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 8: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 9: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 10: hexane; methanol / 14 h / Heating 11: hydrochloric acid / ethanol 12: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 2: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 3: hexane; methanol / 14 h / Heating 4: hydrochloric acid / ethanol 5: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 2: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 3: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 4: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 5: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 6: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 7: hexane; methanol / 14 h / Heating 8: hydrochloric acid / ethanol 9: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 5: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 6: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 8: hexane; methanol / 14 h / Heating 9: hydrochloric acid / ethanol 10: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme