Multi-step reaction with 9 steps
1: 34 percent / 2-methyl-propan-2-ol / 48 h / Heating
2: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 14 h
3: AlCl3, t-BuSH / CH2Cl2 / 0.75 h / 0 °C
4: K2CO3 / dimethylformamide / 14 h / 50 °C
5: 72 percent / 1 N aq. NaOH / methanol; dioxane / 6 h / 50 °C
6: triethylamine / tetrahydrofuran / 0.33 h / -15 - -10 °C
7: NaBH4 / tetrahydrofuran / -10 - 0 °C
8: 82 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 15 h / Ambient temperature
9: 98 percent / hydrazine hydrate / ethanol; dioxane / 0.5 h / Heating
With
sodium hydroxide; sodium tetrahydroborate; aluminium trichloride; sodium hydride; potassium carbonate; hydrazine hydrate; 2-methylpropan-2-thiol; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0968-0896(96)00265-9