Multi-step reaction with 11 steps
1.1: 100 percent / imidazole / dimethylformamide / 60 °C
2.1: 74.5 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / 0 °C
3.1: tert-BuLi / pentane; diethyl ether / 0.5 h / -78 °C
3.2: 51.1 percent / pentane; diethyl ether / 3 h / -78 °C
4.1: 99 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C
5.1: 31.2 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 1.5 h / 20 °C
6.1: 71.4 percent / Zn powder; conc. HCl / acetic acid / 1 h / 80 °C
7.1: 87.5 percent / imidazole / dimethylformamide / 60 °C
8.1: 72.4 percent / N-bromosuccinimide / tetrahydrofuran / 1 h / 0 °C
9.1: tert-BuLi / pentane; diethyl ether / 0.5 h / -78 °C
9.2: 45.3 percent / trisylazide / pentane; diethyl ether / 1 h / -78 °C
10.1: 68.2 percent / H2 / 10 percent Pd-C / ethanol / 3 h / 20 °C
11.1: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; nickel dichloride; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; acetic acid; N,N-dimethyl-formamide; pentane;
DOI:10.3987/COM-00-8952