Multi-step reaction with 8 steps
1: 82 percent / 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: 79 percent / 4-methylmorpholine N-oxide, 4A molecular sieves, tetrapropylammonium perruthenate (TPAP) / CH2Cl2 / 0.5 h / Ambient temperature
6: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature
7: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
8: 1.) AIBN, tri-n-butyltin hydride, 2.) I2 / 1.) 120 deg C - 140 deg C, 3 h, 2.) Et2O, RT, 45 min
With
piperidine; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; copper diacetate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; ammonium acetate; iodine; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane; dichloromethane; acetic acid; benzene;
DOI:10.1021/jm00113a019