formic acid; triethylamine in N,N-dimethyl-formamide

1: NaBH4 / dimethylsulfoxide / 1 h / 20 °C 2: 18 percent / tetra-n-butylammonium chloride, KF*2H2O / dimethylformamide / 4 h View Scheme

1: NaBH4 / dimethylsulfoxide / 1 h / 20 °C 2: 18 percent / tetra-n-butylammonium chloride, KF*2H2O / dimethylformamide / 4 h 3: 98 percent / di-isobutylaluminium hydride / toluene / 2 h / 0 °C View Scheme

1: NaBH4 / dimethylsulfoxide / 1 h / 20 °C 2: 18 percent / tetra-n-butylammonium chloride, KF*2H2O / dimethylformamide / 4 h 3: 98 percent / di-isobutylaluminium hydride / toluene / 2 h / 0 °C 4: 81 percent / MnO2 / CH2Cl2 / 0.5 h View Scheme

1: NaBH4 / dimethylsulfoxide / 1 h / 20 °C 2: 18 percent / tetra-n-butylammonium chloride, KF*2H2O / dimethylformamide / 4 h 3: 98 percent / di-isobutylaluminium hydride / toluene / 2 h / 0 °C 4: 81 percent / MnO2 / CH2Cl2 / 0.5 h 5: 79 percent / toluene-p-sulphonic acid monohydrate / benzene / 17 h / Heating 6: 96 percent / Zn powder / acetic acid / 1.5 h / Ambient temperature 7: 89 percent / tetrahydrofuran / 0.08 h View Scheme