Multi-step reaction with 12 steps
1: m-CPBA / CH2Cl2 / 4 h / Heating
2: 10percent aq. KOH / methanol / 2.5 h / Ambient temperature
3: 99 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h
4: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h
5: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating
6: 73 percent / acetic acid / 0.5 h / Heating
7: 94 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C, 1 h
8: 84 percent / t-BuOK / 2-methyl-propan-2-ol; dimethylformamide / 24 h / Ambient temperature
9: NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) r.t., 2 h
10: NH2NH2*H2O / dimethylformamide / 1 h / Ambient temperature
11: 98 percent / Et3N, DMAP / CH2Cl2 / 3 h / Ambient temperature
12: LiAl(O-t-Bu)3H / tetrahydrofuran / 1 h / 0 °C
With
hydrogenchloride; dmap; potassium hydroxide; n-butyllithium; potassium tert-butylate; sodium hydride; hydrazine hydrate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;