Multi-step reaction with 12 steps
1: 63 percent / CuO, K2CO3, pyridine / 12 h / Heating
2: 80 percent / Cl2, SnCl4 / CH2Cl2 / Ambient temperature
3: NaBH4 / ethanol / 0 °C
4: imidazole / dimethylformamide / Ambient temperature
5: LiAlH4 / tetrahydrofuran / 0 °C
6: MnO2 / benzene / Heating
7: 83 percent / diethyl ether / -78 - 0 °C
8: NaN3 / dimethylformamide / Ambient temperature
9: 240 h / Ambient temperature; pH 4
10: 82 percent / H2 / 10percent Pd/C / ethyl acetate
11: 100 percent / LiOH, H2O / tetrahydrofuran
12: 96 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, N-hydroxybenzotriazole / CH2Cl2 / Ambient temperature
With
pyridine; 1H-imidazole; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; water; hydrogen; chlorine; tin(IV) chloride; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; copper(II) oxide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1039/c39920001693