Methyl iodide → HCID 86592533, compound

HRID 1374437Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH2:5][N:4]1[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13].[H-].[Na+].[CH3:20]I>CN(C=O)C>[CH3:20][O:1][CH2:2][C@H:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH2:5][N:4]1[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

stirringthe mixture was stirred at room temperature for 1 hour
extractionextracted three times with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
customThe solvent was removed in vacuo
customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record: ord-196d99ca7d7b4e0f8c98b092aee7f420
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163936B2

Reaction notes

Loading…