Multi-step reaction with 9 steps
1.1: n-BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 78 percent / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: 98 percent / Et3SiH; TFA / CH2Cl2 / 12 h / 20 °C
3.1: 81 percent / NBS / tetrahydrofuran / 1 h / 0 °C
4.1: 89 percent / t-BuLi / pentane; tetrahydrofuran / 1 h / -78 °C
5.1: 62 percent / NaBH4; NiCl2*6H2O / methanol; tetrahydrofuran / 2 h / Heating
6.1: 59 percent / NBS / tetrahydrofuran / 1 h / 0 °C
7.1: t-BuLi / pentane; tetrahydrofuran / 0.25 h / -78 °C
7.2: 78 percent / trisyl azide / pentane; tetrahydrofuran / 1 h / -78 °C
8.1: 87 percent / TBAF / tetrahydrofuran / 0.08 h / 20 °C
9.1: 97 percent / H2 / 10percent Pd/C / ethanol / 24 h / 20 °C
With
2,2,6,6-tetramethyl-piperidine; triethylsilane; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; trifluoroacetic acid; nickel dichloride;
10percent Pd/C;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; pentane;
DOI:10.1039/b200845a