Methyl Chloride → 3-[4-(3-Cyclopentyloxy-4-cyclopropylmethoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

HRID 1727144Notes

Reaction equation

HRID 1727144 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]3[CH2:18][N:17]([C:19]4[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=4)[C:22]#[N:23])[C:16](=[O:27])[CH2:15]3)[CH:10]=[CH:11][C:12]=2[OH:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH:34]1([CH2:37]Br)[CH2:36][CH2:35]1.CCl>CN(C=O)C.CCOC(C)=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]3[CH2:18][N:17]([C:19]4[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=4)[C:22]#[N:23])[C:16](=[O:27])[CH2:15]3)[CH:10]=[CH:11][C:12]=2[O:13][CH2:37][CH:34]2[CH2:36][CH2:35]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6327Methyl ChlorideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 688283933-[4-(3-Cyclopentyloxy-4-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

Product 1

HCID 688278463-[4-(3-Cyclopentyloxy-4-cyclopropylmethoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrileYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(3-cyclopentyloxy-4-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile (1 mmol), potassium carbonate (2.5 mmol), cyclopropylmethyl bromide (2 mmol) in DMF was created in a dry round bottom flask. The mixture was stirred for 20 h, diluted with EtOAc (or CH3Cl) and filtered through celite. The filtrate was washed with water and then brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give pure product. Yield: 83%.

Workup

  1. customwas created in a dry round bottom flask
  2. filtrationfiltered through celite
  3. washThe filtrate was washed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. customto give pure product

Sources & evidence

ORD record
ord-2d96a059ef9c4733883679aa4aff99e5
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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