Phenol → 3-[4-(4-Benzyloxy-3-cyclopentyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

HRID 1727142Notes

Reaction equation

HRID 1727142 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)=[CH:11][C:10]=1[O:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[C:31]#[N:32].C1(O)C=CC=CC=1.N(C)(C)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][N:18]([C:28]3[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=3)[C:31]#[N:32])[C:17](=[O:20])[CH2:16]2)=[CH:11][C:10]=1[O:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 1146TrimethylamineHCID 233813-BromobenzonitrileHCID 688300864-(4-Benzyloxy-3-cyclopentyloxyphenyl)pyrrolidin-2-one

Product 1

HCID 688288793-[4-(4-Benzyloxy-3-cyclopentyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(4-benzyloxy-3-cyclopentyloxyphenyl)pyrrolidin-2-one, 3-bromobenzonitrile, phenol (0.1 mmol), copper acetate (0.15 mmol), arylboronic acid (0.12 mmol), 4 Å Molecular Sieves (“MS”) (˜100 mg) and CH2Cl2 (1 mL) was created in a dry round bottom flask. (CH3)3N (0.22 mmol) was added, the flask was sealed, and the mixture was stirred for 24 h. The reaction mixture was then diluted with 10 mL of CH2Cl2 and filtered. The filtrate was washed with saturated NH4Cl, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel or preparative liquid chromatography-mass spectrometry LC-MS to give pure product. Yield: 74%.

Workup

  1. customwas created in a dry round bottom flask
  2. customthe flask was sealed
  3. filtrationfiltered
  4. washThe filtrate was washed with saturated NH4Cl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel or preparative liquid chromatography-mass spectrometry LC-MS
  8. customto give pure product

Sources & evidence

ORD record
ord-57db761b25d54e32b04e7b39a2187a60
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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