Multi-step reaction with 8 steps
1: 36 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature
2: 98 percent / pyridine / 1.) room temp., 30 min, 2.) 80 deg C, 2 h
3: 87 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature
4: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 40 h / Ambient temperature
5: aq. HCl / methanol / 5 h / Ambient temperature
6: 96 percent / pyridine / 3 h / Ambient temperature
7: 1.) NaH, 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) DMF, room temp., 2 h, 2.) DMF, THF, 60 deg C oil bath, 20 h
8: NH3 gas / methanol / 48 h / 80 °C
With
pyridine; hydrogenchloride; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); ammonia; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo9603542