benzyl 4-(2,3-dichlorophenyl)pyridine-1(4H)-carboxylate → HCID 66632347, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of intermediate 45 (7.0 g, 19.5 mmol) in toluene (150 mL) was added RhCl (PPh3)3 (2.1 g, 2.0 mmol) as a slurry in toluene (50 mL). The reaction was subjected to an atmosphere of H2 at 40 psi and heated to 70° C. After 6 h, the reaction was filtered through silica gel and the silica gel was washed with 1:9 EtOAc/toluene. The filtrate was dissolved in toluene, concentrated in vacuo, and purified by flash chromatography on silica gel column (elution with PE/EtOAc=50:1) to give benzyl 4-(2,3-dichlorophenyl)piperidine-1-carboxylate (intermediate 46) (6.8 g, 96%) as an oil. HPLC: 99%, RT 30843 min. MS (ESI) m/z 386.1 [M+NA]+.

Provenance & Evidence