potassium tert-butylate; isopentyl nitrite in toluene T=-20 - 0°C; 0.5 h;

1: NH3 / methanol / 2 h / Heating 2: 93 percent / Aliquat 336, 50percent aq. NaOH / toluene / 4 h / 20 - 25 °C 3: 81.6 percent / t-BuOK, isoamyl nitrite / toluene / 0.5 h / -20 - 0 °C View Scheme

1: 97 percent / CH2Cl2; H2O / 3 h / -10 - 25 °C 2: NH3 / methanol / 2 h / Heating 3: 93 percent / Aliquat 336, 50percent aq. NaOH / toluene / 4 h / 20 - 25 °C 4: 81.6 percent / t-BuOK, isoamyl nitrite / toluene / 0.5 h / -20 - 0 °C View Scheme

1: 93 percent / Aliquat 336, 50percent aq. NaOH / toluene / 4 h / 20 - 25 °C 2: 81.6 percent / t-BuOK, isoamyl nitrite / toluene / 0.5 h / -20 - 0 °C View Scheme

1: H2 / 5percent Ru/C / methanol / 24 h / 68 - 74 °C / 2068.6 Torr 2: 90 g / 1-hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 0.25 h / pH = 9.5 3: HCl(g) / ethyl acetate / 0.5 h / 0 °C 4: 1) PhCNS; 2) CF3CO2H / 1) CH2Cl2, reflux, 20 min; 2) 50 deg C, 20 min View Scheme