1: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 2: 100 percent / 48percent aq. HF / acetonitrile / 1 h 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 4: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 5: 64 percent / toluene / 10 h / Heating 6: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 7: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

With  ammonia; lithium in  tetrahydrofuran T=-78°C; 0.5 h;   

With  pyridine 9 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: 91 percent / pyridine / CH2Cl2 / 0.5 h2: 91 percent / pyridine / 9 h / Ambient temperature  

Multi-step reaction with 7 steps 1: 1.) lithium diisopropyl amide / tetrahydrofuran / -78 °C2: toluene / 10 h / Heating3: 48percent aq. HF / 1.5 h / 0 °C4: diethyl ether / 0 °C5: LiAlH4 / diethyl ether / 3 h6: 91 percent / pyridine / CH2Cl2 / 0.5 h7: 91 percent / pyridine / 9 h / Ambient temperature  

Multi-step reaction with 4 steps 1: diethyl ether / 0 °C2: LiAlH4 / diethyl ether / 3 h3: 91 percent / pyridine / CH2Cl2 / 0.5 h4: 91 percent / pyridine / 9 h / Ambient temperature  

Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether / 3 h2: 91 percent / pyridine / CH2Cl2 / 0.5 h3: 91 percent / pyridine / 9 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 48percent aq. HF / 1.5 h / 0 °C2: diethyl ether / 0 °C3: LiAlH4 / diethyl ether / 3 h4: 91 percent / pyridine / CH2Cl2 / 0.5 h5: 91 percent / pyridine / 9 h / Ambient temperature  

With  ammonia; lithium in  tetrahydrofuran T=-78°C; 0.5 h;