Multi-step reaction with 12 steps
1: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min
2: oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
3: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C
4: 60 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
5: hydrazine hydrate / ethanol / 2.5 h / Heating
6: aq. Na2CO3 / CH2Cl2 / 3 h / Heating
7: 80 percent / aq. Na2CO3 / CH2Cl2 / 0.08 h / 0 °C
8: 60 percent / O2, PdCl2, CuCl2 / dimethylformamide; H2O / 0.67 h / 70 °C
9: 94 percent / H2 / 10percent Pd/C / methanol / 1 h
10: 55 percent / diisopropylethylamine / CH2Cl2 / 120 h / Ambient temperature
11: 94 percent / concentrated HCl / methanol / 0.5 h / Heating
12: 84 percent / diisopropylethylamine / CH2Cl2 / 2 h / Heating
With
hydrogenchloride; oxalyl dichloride; hydrogen; oxygen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper dichloride; palladium dichloride; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00186a038