methanol; Dowex 1-X8 (OH(1-)) T=0°C; 2 h;

1: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 2: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 1.) N-bromoacetamide, water, 2.) silver oxide / 1) acetone, irradiation, 60 min; 2) dimethoxyethane, reflux, 1 h 2: 64 percent / m-chloroperbenzoic acid, lithium carbonate, 4,4'-thiobis(2-tert-butyl-6-methylphenol) / CH2Cl2 / 168 h / Heating 3: 100 percent / aq. sodium hydroxide / tetrahydrofuran / 1 h 4: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h 5: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 6: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 7: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 8: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 9: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 10: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 11: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 12: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 64 percent / m-chloroperbenzoic acid, lithium carbonate, 4,4'-thiobis(2-tert-butyl-6-methylphenol) / CH2Cl2 / 168 h / Heating 2: 100 percent / aq. sodium hydroxide / tetrahydrofuran / 1 h 3: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h 4: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 5: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 6: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 7: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 8: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 9: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 10: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 11: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h 2: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 3: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 4: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 5: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 6: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 7: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 8: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 9: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 2: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 3: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 2: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 100 percent / aq. sodium hydroxide / tetrahydrofuran / 1 h 2: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h 3: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 4: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 5: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 6: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 7: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 8: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 9: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 10: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 3: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 4: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 5: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 6: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 7: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme

1: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 2: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 3: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 4: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 5: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 6: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme