in diethyl ether; water

sodium carbonate in acetone 12 h; Yield given;

in tetrahydrofuran; diethyl ether 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature; Yield given;

1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature View Scheme

1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 3: TFA / CH2Cl2 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

hydrogenchloride; palladium monocarbide in 1,4-dioxane

palladium on activated charcoal; ethanol Hydrogenation;

1: HNO3, Ac2O 2: hydrogen, Na2CO3 / Pd-C / H2O; diethyl ether View Scheme

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature View Scheme

piperidine in N,N-dimethyl-formamide T=20°C; 0.0833333 h;