Multi-step reaction with 13 steps
1: 86 percent / conc. HCl / 24 h / Heating
2: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature
3: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
4: toluene / 24 h / Heating
5: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
6: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
9: 80 percent / 0.67 h / 105 - 110 °C
10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
With
hydrogenchloride; 1-hydroxy-2(1H)-pyridinethione; dmap; sodium hydroxide; sodium periodate; oxalyl dichloride; hydrogen; dihydrogen peroxide; sodium cyanoborohydride; sodium carbonate; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo980153t