Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Reflux
3.1: 20% palladium hydroxide on charcoal; hydrogen / ethyl acetate / 10 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.58 h / 0 - 20 °C
4.2: 14.08 h / 0 - 20 °C
5.1: hydrogenchloride / methanol; water / 29 h / 20 °C
6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 45 h / 20 °C
7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 2.33 h / -78 °C
8.1: tert.-butyl lithium; 9-methoxy-9-BBN / tetrahydrofuran; diethyl ether; hexane; pentane / 1.17 h / -78 - 20 °C
8.2: 50 °C
9.1: 2,3-Dimethyl-2-butene; dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C
9.2: 0 - 20 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium aluminium tetrahydride; 2,3-Dimethyl-2-butene; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 20% palladium hydroxide on charcoal; hydrogen; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydride; N-ethyl-N,N-diisopropylamine; 9-methoxy-9-BBN;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; pentane;
8.2: Suzuki-Miyaura coupling;
DOI:10.1002/chem.201101437