hydrogenchloride 1 h; Heating;

1: acetic acid, sodium acetate / H2O 2: Zn, acetic acid 3: cc. HCl / dimethylformamide 4: 2 M HCl / Heating 5: 76 percent / 1 M HCl / Heating View Scheme

1: Zn, acetic acid 2: cc. HCl / dimethylformamide 3: 2 M HCl / Heating 4: 76 percent / 1 M HCl / Heating View Scheme

1: 73 percent / t-butylhydroperoxide / VO(acac)2 / toluene 2: 60 percent / tetrabutylammonium iodide 3: 30 percent / KHF2 / ethane-1,2-diol / 160 °C 4: 56 percent / ethyldiisopropylamine / CH2Cl2 5: hydrogen, H(1+) / Pd/C / ethyl acetate 6: triethylamine, 4-dimethylaminopyridine 7: 18 percent / potassium carbonate / dimethylsulfoxide / 80 °C 8: 1 M HCl / Heating View Scheme

1: tritilation 2: 73 percent / t-butylhydroperoxide / VO(acac)2 / toluene 3: 60 percent / tetrabutylammonium iodide 4: 30 percent / KHF2 / ethane-1,2-diol / 160 °C 5: 56 percent / ethyldiisopropylamine / CH2Cl2 6: hydrogen, H(1+) / Pd/C / ethyl acetate 7: triethylamine, 4-dimethylaminopyridine 8: 18 percent / potassium carbonate / dimethylsulfoxide / 80 °C 9: 1 M HCl / Heating View Scheme

1: 88 percent / Et3N / butan-1-ol / 24 h / Heating 2: NaOAc, AcOH / H2O / Ambient temperature 3: 74.5 percent / Zn, NH4Cl / tetrahydrofuran; methanol / 0.5 h 4: 1.) concd aq. HCl, 2.) 0.6 N aq. HCl / 1.) DMF, 3.5 h, 2.) rt, 30 min 5: 76 percent / 1 N aq. HCl / 1 h / Heating View Scheme

1: cc. HCl / dimethylformamide 2: 2 M HCl / Heating 3: 76 percent / 1 M HCl / Heating View Scheme