1: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 2: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 3: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

Multi-step reaction with 6 steps 2: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C3: Jones reagent / acetone / 0 °C4: diethyl ether / 0 °C5: 98 percent / KF*2H2O / dimethylformamide / 25 °C6: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C  

Multi-step reaction with 7 steps 1: 100 percent / NaI / acetone / Heating3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C4: Jones reagent / acetone / 0 °C5: diethyl ether / 0 °C6: 98 percent / KF*2H2O / dimethylformamide / 25 °C7: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C  

Multi-step reaction with 2 steps 1: 98 percent / KF*2H2O / dimethylformamide / 25 °C2: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C  

Multi-step reaction with 4 steps 1: Jones reagent / acetone / 0 °C2: diethyl ether / 0 °C3: 98 percent / KF*2H2O / dimethylformamide / 25 °C4: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C