Multi-step reaction with 8 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
1.2: 2 h / -78 - 20 °C / Inert atmosphere
2.1: sulfuric acid; acetic acid / water / 16 h / 0 - 120 °C / Inert atmosphere; Reflux
3.1: sulfuric acid; sodium nitrite / water; acetonitrile / 20 °C / Inert atmosphere
4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
6.1: thionyl chloride / 85 °C / Inert atmosphere
7.1: ammonia / chloroform / 20 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere
With
2,2,6,6-tetramethyl-piperidine; n-butyllithium; thionyl chloride; oxalyl dichloride; sulfuric acid; ammonia; acetic acid; triethylamine; N,N-dimethyl-formamide; sodium nitrite;
In
tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1021/jo2025724