Multi-step reaction with 9 steps
1: piperidine, HOAc / benzene / 22 h / Heating
2: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, 1.5 h
3: NH4OAc, Cu(OAc)2 / acetic acid / 24 h / Heating
4: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature
5: oxalyl chloride, DMSO / CH2Cl2; tetrahydrofuran / 0.25 h / -78 °C
6: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature
7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min
8: HOAc, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature
9: 1N aq. NaOH / dioxane / 18 h / Ambient temperature
With
piperidine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; benzene;
DOI:10.1021/jm00113a019