Multi-step reaction with 11 steps
1: 86 percent / 15 h / 112 °C
2: 80 percent / NaH / dimethylformamide / 36 h / 20 °C
3: 84 percent / Na; MeOH / 1 h / 0 °C
4: 67 percent / lithium diisopropylamide / tetrahydrofuran / 4 h / -70 - -60 °C
5: 87 percent / [NO2]BF4 / CH2Cl2 / 16 h / 0 - 20 °C
6: 81 percent / NaBH4 / methanol; tetrahydrofuran / 4 h / 0 - 5 °C
7: 77 percent / p-toluenesulfonic acid / 24 h / 20 °C
8: 72.3 percent / N-bromosuccinimide / benzene / 26 h / 20 °C
9: 85 percent / NaN3 / dimethylformamide / 16 h / 70 - 75 °C
10: 86 percent / aq. Na2S2O7 / tetrahydrofuran / 25 h / 20 °C
11: 70 mg / sodium cyanoborohydride; AcOH / 1,2-dichloro-ethane / 35 h
With
methanol; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; nitronium tetrafluoborate; sodium pyrosulfate; sodium; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0968-0896(03)00271-2