Multi-step reaction with 9 steps
1: 98 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, 0 deg C, 90 min, 2.) THF, a) -78 deg C, 90 min, b) 0 deg C, 2 h
3: HCl, AcOH / 9 h / Heating
4: SOCl2 / 6 h / Ambient temperature
5: CH2Cl2 / 36 h / Ambient temperature
6: 59 percent / LiBH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 48 h
7: 94 percent / H2 / 10percent Pd/C / ethanol / 7 h / Ambient temperature
8: 80 percent / tetrahydrofuran / 6 h / Ambient temperature
9: 89 percent / BH3 / tetrahydrofuran / 4 h / 0 °C
With
hydrogenchloride; lithium borohydride; n-butyllithium; thionyl chloride; borane; hydrogen; sodium hydride; acetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja953578v