sodium methylate; tetra-(n-butyl)ammonium iodide in methanol T=40°C; 3 h;

1: With sodium methylate; tetra-(n-butyl)ammonium iodide in methanol T=40°C; 24 h; 2: With hydrogenchloride in methanol; water

1: With sodium hydroxide; sodium iodide in methanol 2: With sodium hypochlorite in methanol T=4°C; 2 h; Further stages.;

1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine in dichloromethane T=20°C;

1: 89 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl3 / a) 0 deg C, 1 h, b) RT, overnight 2: 94 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 2 h 3: 60 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl3 / a) 0 deg C, 1 h, b) RT, overnight 4: 80 percent / 1 N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 20 h 5: 90 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl3 / a) 0 deg C, 1 h, b) RT, 20 h 6: 85 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 20 h 7: 90 percent / TFA, HCl / a) 0 deg C, 30 min, b) RT, 30 min View Scheme

tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide

sodium hydroxide in water Acetylation; 0.333333 h;

1: 60 percent / DCC / acetonitrile / -10 °C 2: 36 percent / hydrazine hydrate / methanol / Ambient temperature 3: isopentyl nitrite 4: 46 percent / dimethylformamide / 4 °C View Scheme

1: 72 percent / 1-hydroxybenzotriazol, dicyclohexylcarbodiimide / dimethylformamide / 1 h / 0 °C 2: hydrogen / palladium black / 2-methyl-propan-2-ol / 8 h 3: dicyclohexylcarbodiimide / CHCl3 / 3 h / -20 - 0 °C / r.t., overnight 4: 86 percent / hydrogen / palladium black / 2-methyl-propan-2-ol / 16 h 5: 57 percent / 1-hydroxybenzotriazol, dicyclohexylcarbodiimide / dimethylformamide / 1 h / -20 - 0 °C / O deg C, overnight 6: ammonium formate / 10percent palladium on carbon / methanol / 3 h / Ambient temperature 7: anisol, trifluoroacetic acid / 1 h / Ambient temperature View Scheme

1: N-methylmorpholine / tetrahydrofuran / 0.03 h / 20 °C 2: 1H-tetrazole / tetrahydrofuran / 0.33 h / 20 °C 3: I2, H2O / tetrahydrofuran / 0.17 h / -40 °C 4: 30percent aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme