Ethyl 5-benzylnicotinate → Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate

Participants

Reaction Steps

A suspension of ethyl-5-benzylnicotinate (1.0 g, 4.1 mmol) and PtO2 (800 mg) in EtOH (25 mL) and HCl (conc., 5.0 mL) was mixed in a Parr shaker under 40 psi of H2 for 2 hours. The mixture was filtered through celite and concentrated to about 10% of the original volume. The resulting mixture was extracted with CH2Cl2 (3×30 mL). The organic layer was concentrated under reduced pressure to furnish the title compound (755 mg, 73% yield) as a white solid. MS m/z: 254.3 (M+1).

Provenance & Evidence