1: With sulfuric acid in tetrahydrofuran; water 2: With hydrogen; palladium 10 on activated carbon in tetrahydrofuran; water T=30°C; P=3102.97 Torr; 26.5 h; 3: With sodium hydroxide in tetrahydrofuran; water pH=7.24; 0.5 h;

ammonium formate; palladium in ethanol; water; ethyl acetate

copper(l) iodide; ethyl acetate in methanol; N,N-dimethyl-formamide T=110°C; 8 h;

1.1: HCl / CH2Cl2; diethyl ether / 0.5 h / 20 °C 1.2: 82 percent / BF3*SMe2 / CH2Cl2 / 5 h / 20 °C 2.1: 85 percent / CuI; ethyl acetate / dimethylformamide; methanol / 8 h / 110 °C View Scheme

1.1: 95 percent / N-bromoacetamide / CH2Cl2 / 2 h / 20 °C 2.1: 65 percent / TFA; aq. H2O2 / CH2Cl2 / 2 h / 20 °C 3.1: NaH / dimethylformamide / 0.33 h 3.2: 94 percent / dimethylformamide / 1 h / 20 °C 4.1: HCl / CH2Cl2; diethyl ether / 1 h 4.2: 85 percent / TMSCl; Ph3P / tetrahydrofuran / 8 h / Heating 5.1: HCl / CH2Cl2; diethyl ether / 0.5 h / 20 °C 5.2: 82 percent / BF3*SMe2 / CH2Cl2 / 5 h / 20 °C 6.1: 85 percent / CuI; ethyl acetate / dimethylformamide; methanol / 8 h / 110 °C View Scheme

1.1: KOH / ethanol 1.2: 89 percent / ethanol; ethyl acetate / 20 °C 2.1: 30 percent / PPA / 6 h / Heating 3.1: 95 percent / N-bromoacetamide / CH2Cl2 / 2 h / 20 °C 4.1: 65 percent / TFA; aq. H2O2 / CH2Cl2 / 2 h / 20 °C 5.1: NaH / dimethylformamide / 0.33 h 5.2: 94 percent / dimethylformamide / 1 h / 20 °C 6.1: HCl / CH2Cl2; diethyl ether / 1 h 6.2: 85 percent / TMSCl; Ph3P / tetrahydrofuran / 8 h / Heating 7.1: HCl / CH2Cl2; diethyl ether / 0.5 h / 20 °C 7.2: 82 percent / BF3*SMe2 / CH2Cl2 / 5 h / 20 °C 8.1: 85 percent / CuI; ethyl acetate / dimethylformamide; methanol / 8 h / 110 °C View Scheme