Multi-step reaction with 9 steps
1: sodium hydroxide / tetrahydrofuran; ethanol; water / 3 h / Reflux
2: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C
3: sodium tetrahydroborate / tetrahydrofuran; 1,2-dimethoxyethane / 1 h / 0 °C
4: thionyl chloride / toluene / 2 h / Reflux
5: N,N-dimethyl-formamide / 6 h / 20 °C
6: hydrazine hydrate / ethanol / 1 h / Reflux
7: tetrahydrofuran / 1 h / 20 °C
8: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 2 h / 20 °C
9: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 10 h / 80 °C
With
sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; 5%-palladium/activated carbon; hydrogen; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; sodium hydroxide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2011.06.059