1: NaNO2 / acetic acid; H2O / Ambient temperature 2: 59 percent / NH3 / methanol / Ambient temperature 3: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature 4: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h 5: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature 6: 72 percent / NH3 / methanol / Ambient temperature View Scheme

Multi-step reaction with 5 steps 1: NaNO2 / acetic acid; H2O / Ambient temperature2: 59 percent / NH3 / methanol / Ambient temperature3: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature4: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h5: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature