Multi-step reaction with 12 steps
1: 1.) Mg / 1.) Et2O, 2.) Et2O, room temp., 14 h
2: 95 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
3: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C
4: 51 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
5: 76 percent / H2 / 10percent Pd/C / methanol / 3 h
6: 86 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
7: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min
8: hydrazine hydrate / ethanol / 2 h / Heating
9: aq. Na2CO3 / CH2Cl2 / 0.08 h / 0 °C
10: 80 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
11: 0.14 M Zn(BH4)2 / diethyl ether / 0.75 h / 0 °C
12: triethylamine / CH2Cl2 / 0.17 h / 0 °C
With
zinc(II) tetrahydroborate; oxalyl dichloride; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038