Multi-step reaction with 6 steps
1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl
2: 73 percent / ethanol / 4 h / Heating
3: 1.) NaCNBH3, p-TsOH, 2.) aq. NaOH / 1.) THF, RT, 37 h, 2.) THF, reflux, 3.5 h
4: 74 percent / propan-2-ol / 16 h / Heating
5: HCO2H / 4 h / Ambient temperature
6: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) DMF, 0 deg C, 20 min, 2.) DMF, overnight
With
hydrogenchloride; sodium hydroxide; formic acid; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); iodine; diisobutylaluminium hydride; sodium cyanoborohydride; O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; magnesium; N-ethyl-N,N-diisopropylamine;
In
ethanol; isopropyl alcohol;
DOI:10.1021/jm970873c