Methyl iodide → HCID 66750656, compound

Participants

Reaction Steps

Methyl iodide (4.00 mL, 64.2 mmoles) was added to a room temperature solution of (S)-2-[(S)-1-tert-Butoxycarbonyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (1.39 g, 2.88 mmoles) and cesium carbonate (1.87 g, 5.75 mmoles) in DMF (10 mL) and the mixture stirred at room temperature for 4 days. The reaction mixture was diluted with EtOAc (200 mL) and washed with brine (3×200 mL). The aqueous layers were re-extracted with EtOAc (2×200 mL). The organic layers were dried (Na2SO4), combined, and concentrated in vacuo to give a yellow oil. Purification of the residue by flash chromatography, eluting with 0-10% EtOAc/CH2Cl2 afforded 0.71 g (50% yield) of (S)-2-[(S)-1-tert-Butoxycarbonyl-2-(4-methoxy-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester, as a colorless oil.

Provenance & Evidence