Multi-step reaction with 12 steps
1: 96 percent / HBr; AcOH / H2O / 8 h / Heating
2: 85 percent / NaH / dimethylformamide
3: 95 percent / pyridine / CH2Cl2 / 0 - 20 °C
4: 80 percent / dimethylformamide / 1 h
5: 94 percent / NaBH4 / tetrahydrofuran / 0.08 h / 0 °C
6: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / 20 °C
7: 38 percent / DIBAL-H / toluene / 0.25 h / 0 °C
8: 64 percent / NaH / dimethylformamide / 20 °C
9: 90 percent / 2,6-lutidine / CH2Cl2 / 0.33 h / 0 °C
10: 99 percent / H2 / Raney-Ni / methanol; tetrahydrofuran / 8.5 h
11: 95 percent / K2CO3 / CH2Cl2 / 1 h / 0 °C
12: 87 percent / KH / dimethylformamide / 1 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; hydrogen bromide; hydrogen; potassium hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid;
nickel;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja0013879