Benzyl Alcohol → Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 4-(2-formylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (305 mg, 1.06 mmol, 1 eq.)), 5% Pd/C (30 mg) and EtOAc (10 mL) was stirred at room under 1 atm of H2 for 18 h. Mainly benzyl alcohol was observed by LC/MS and HPLC (Rt=4.21 min). The catalyst was filtered off, the filtrate was concentrated in vacuo, and purified by ISCO chromatography (24 g, Si35, 10 to 25% EtOAC in Hexanes, Rf˜0.6 in 1:1 Hex:EtOAc, to give 432 mg (52%) of tert-butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate as a thick, colorless oil.

Provenance & Evidence