106-52-5

1445-73-4

106-52-5

The general procedure for the synthesis of 1-methyl-4-piperidinol from N-methyl-4-piperidone was as follows: in standard experiments, the catalyst complex 1 (6.1 mg, 10 mol%) and the hydrogenation reagent H[BAr'4]-(Et2O)2 (10.1 mg, 10 mol%) were dissolved in a 100 mL thick-walled glass reactor fitted with a TEFLON stopper and stirring bar of THF (2.0 mL). Subsequently, the substrate to be hydrogenated (0.5 mmol) was added. The reaction system was degassed by a freeze-pump-thaw cycle and then charged with hydrogen (1 or 4 atm). The reaction mixture was stirred at a set temperature (25-60 °C) until the reaction was complete. At the end of the reaction, the solvent was removed by evaporation and the residue was initially purified by passing through a silica gel column. After removal of solvent under reduced pressure, the crude product was dissolved in CDCl3 and analyzed by 1H NMR. The final product was further purified by column chromatography or preparative thin layer chromatography (TLC) using hexane/ethyl acetate (3:1, v/v) as eluent. The purified products were characterized by 1H NMR and GC-MS, and the spectral data were consistent with those reported in the literature or real samples.