Methyl iodide → 3-(3-cyclopentyloxy-4-methoxy-N-methylanilino)-2-cyclopenten-1-one
Reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[NH:10][C:11]2[CH2:15][CH2:14][C:13](=[O:16])[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[N:10]([C:11]2[CH2:15][CH2:14][C:13](=[O:16])[CH:12]=2)[CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
5
Procedure
0.10 g (0.35 mmole) of 3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one produced in Example 1, 0.02 g of sodium hydride (60%), and 0.06 g (0.42 mmole) of methyl iodide were dissolved in 4 ml of N,N-dimethylformamide and the solution was stirred at room temperature for one night. The reaction solution was quenched with water, then was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo to obtain a crude product. The crude product was purified by flash chromatography (SiO2; eluted by 2% methanol/methylene chloride) to obtain the title compound 0.10 g (yield 93.4%) as a colorless solid.
Workup
- customThe reaction solution was quenched with water
- extractionwas extracted with methylene chloride
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customthe solvent was removed in vacuo
- customto obtain a crude product
- customThe crude product was purified by flash chromatography (SiO2; eluted by 2% methanol/methylene chloride)
Sources & evidence
- ORD record
- ord-3aba3563d5884ff3ad3519827a91a041
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235736B1
Reaction notes
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