Methyl iodide → HCID 131729316, compound

Participants

Reaction Steps

To cis-phenylmethyl (3RS,5SR)-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-hydroxy-1-piperidinecarboxylate (380 mg, 0.96 mmol) in 5 mL of CH2Cl2 was added iodomethane (1 mL, 16.1 mmol) and Ag2O (1.15 g, 5.0 mmol). The reaction was allowed to stir at room temperature under nitrogen for 48 h. The reaction mixture was filtered through a pad of Celite® which was washed with 25 mL CH2Cl2, and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel using a 10-100% EtOAc/hexanes gradient to provide the desired compound (210 mg; 53%) as a colorless oil.

Provenance & Evidence