Methyl iodide → HCID 86592533, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-allyl 3-methyl (2R)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (234 mg, 0.97 mmol) in DMF (4.7 ml) was added at 0° C. sodium hydride (60% suspension in oil, 39 mg, 0.98 mmol) and the mixture was stirred for 30 minutes. Then thereto was added at 0° C. methyl iodide (0.95 ml, 9.7 mmol) and the mixture was stirred at room temperature for 1 hour. After cooled to 0° C., the reaction mixture was poured into ice water and extracted three times with ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified with silica gel chromatography to give 1-allyl 3-methyl (2R)-2-(methoxymethyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (55 mg, 15%).

Provenance & Evidence