sodium tetrahydroborate

lithium hydroxide in tetrahydrofuran; water T=25°C;

1: 95 percent / imidazole / dimethylformamide / 0 - 25 °C 3: 100 percent / NaI / acetone / Heating 5: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 6: Jones reagent / acetone / 0 °C 7: diethyl ether / 0 °C 8: 98 percent / KF*2H2O / dimethylformamide / 25 °C 9: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 10: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 11: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 12: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

2: 100 percent / NaI / acetone / Heating 4: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 5: Jones reagent / acetone / 0 °C 6: diethyl ether / 0 °C 7: 98 percent / KF*2H2O / dimethylformamide / 25 °C 8: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 9: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 10: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 11: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 2: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 3: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 4: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

2: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 3: Jones reagent / acetone / 0 °C 4: diethyl ether / 0 °C 5: 98 percent / KF*2H2O / dimethylformamide / 25 °C 6: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 7: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 8: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 9: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 100 percent / NaI / acetone / Heating 3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 4: Jones reagent / acetone / 0 °C 5: diethyl ether / 0 °C 6: 98 percent / KF*2H2O / dimethylformamide / 25 °C 7: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 8: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 9: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 10: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 98 percent / KF*2H2O / dimethylformamide / 25 °C 2: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 3: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 4: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 5: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: Jones reagent / acetone / 0 °C 2: diethyl ether / 0 °C 3: 98 percent / KF*2H2O / dimethylformamide / 25 °C 4: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 5: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 6: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 7: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

1: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 2: Jones reagent / acetone / 0 °C 3: diethyl ether / 0 °C 4: 98 percent / KF*2H2O / dimethylformamide / 25 °C 5: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 6: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 7: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 8: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme