hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 5 h; Ambient temperature;

1: 22 percent / HNO3, H2SO4 / 0.83 h / Heating 2: H2 / 10percent Pd/C / ethanol; ethyl acetate / 48 h / 836 Torr View Scheme

triethylamine in diethyl ether; acetonitrile 1.) 40 deg C, 10 min, 2.) RT, 25 h, 3.) 40 deg C, 4 h;

triethylamine in acetonitrile 1.) 40 deg C, 10 min, 2.) RT, 25 h, 3.) 40 deg C, 4 h;

1: With N-ethyl-N,N-diisopropylamine in DMF (N,N-dimethyl-formamide) T=60°C; 3 h; 2: With sodium hydroxide in methanol T=60°C; 1 h; 3: With hydrogenchloride in methanol; water T=0°C; pH=2;

1: 94 percent / Et3N / acetonitrile; diethyl ether / 1.) 40 deg C, 10 min, 2.) RT, 25 h, 3.) 40 deg C, 4 h 2: 94 percent / aq. NaOH / 1.) 60 deg C, 15 min, 2.) RT, 1 h View Scheme

1: Et3N / CH2Cl2 / 6 h / Ambient temperature 2: 89 percent / 1 M LiOH / ethanol / 2 h 3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCI) / dimethylformamide / 12 h / Ambient temperature 4: HCl(g) / 2 h / 0 - 20 °C 5: ammonia / ethanol / 8 h / Ambient temperature 6: H2 / 10percent Pd/C / methanol / 4 h / 2280 Torr / Ambient temperature 7: formic acid / 12 h / Ambient temperature View Scheme