hydrogen; platinum(IV) oxide in ethanol

1.1: 82 percent / K2CO3; LiCl / Pd(OAc)2 / dimethylformamide / 72 h / 100 °C 2.1: 91 percent / aq. HCl / tetrahydrofuran 3.1: NaOH / ethanol 3.2: triphosgene / tetrahydrofuran / 45 °C 3.3: 84 percent / HCl / diethyl ether / 24 h 4.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 5.1: CH3COOH / CH2Cl2 / 24 h 5.2: 90 percent / TFA / CH2Cl2 / 0.5 h 6.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 6.2: m-CPBA / CH2Cl2 / -78 °C 6.3: 64 percent / Na2CO3 / toluene / Heating 7.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 8.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 9.1: DMAP / tetrahydrofuran / 91 h View Scheme

sodium cyanoborohydride; acetic acid in methanol T=20 - 90°C; 6 h;

1.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 2.1: CH3COOH / CH2Cl2 / 24 h 2.2: 90 percent / TFA / CH2Cl2 / 0.5 h 3.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 3.2: m-CPBA / CH2Cl2 / -78 °C 3.3: 64 percent / Na2CO3 / toluene / Heating 4.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 5.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 6.1: DMAP / tetrahydrofuran / 91 h View Scheme

1.1: CH3COOH / CH2Cl2 / 24 h 1.2: 90 percent / TFA / CH2Cl2 / 0.5 h 2.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 2.2: m-CPBA / CH2Cl2 / -78 °C 2.3: 64 percent / Na2CO3 / toluene / Heating 3.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 4.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 5.1: DMAP / tetrahydrofuran / 91 h View Scheme

1.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 1.2: m-CPBA / CH2Cl2 / -78 °C 1.3: 64 percent / Na2CO3 / toluene / Heating 2.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 3.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 4.1: DMAP / tetrahydrofuran / 91 h View Scheme

1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 2: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 3: DMAP / tetrahydrofuran / 91 h View Scheme

1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 2: DMAP / tetrahydrofuran / 91 h View Scheme

1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 2: DMAP / tetrahydrofuran / 91 h View Scheme

1.1: 91 percent / aq. HCl / tetrahydrofuran 2.1: NaOH / ethanol 2.2: triphosgene / tetrahydrofuran / 45 °C 2.3: 84 percent / HCl / diethyl ether / 24 h 3.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 4.1: CH3COOH / CH2Cl2 / 24 h 4.2: 90 percent / TFA / CH2Cl2 / 0.5 h 5.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 5.2: m-CPBA / CH2Cl2 / -78 °C 5.3: 64 percent / Na2CO3 / toluene / Heating 6.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 7.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 8.1: DMAP / tetrahydrofuran / 91 h View Scheme