Multi-step reaction with 12 steps
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
With
pyridine; 1H-imidazole; methanol; dmap; sodium hydroxide; thionyl chloride; Dowex 1-X8 (OH(1-)); Dowex 50W-X8 (H+); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; water; lithium carbonate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; diborane; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; N-bromoacetamide;
In
tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00538a030