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

HRID 1819340Notes

Reaction equation

HRID 1819340 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][N:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])[C:17](=[O:28])[CH2:16]2)=[CH:11][C:10]=1[O:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)C1C=CC=CC=1>CCO.CCOC(C)=O.[Pd]>[CH:30]1([O:29][C:10]2[CH:11]=[C:12]([CH:15]3[CH2:19][N:18]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[C:17](=[O:28])[CH2:16]3)[CH:13]=[CH:14][C:9]=2[OH:8])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 1

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

Product 1

HCID 688283933-[4-(3-Cyclopentyloxy-4-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrileYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

200 mg of Pd—C was added to 3-[4-(4-benzyloxy-3-cyclopentyloxyphenyl)-2-oxo-pyrrolidin-1-yl]-benzonitrile (1.7 g. 3.8 mmol) in EtOH/EtOAc and flushed with H2 three times. The mixture was then stirred under H2 at r.t. for 72 h. The mixture was filtered through celite and then concentrated under reduced pressure. The residue was then dissolved in EtOAc and washed with 2N HCl, sat. NaHCO3, and sat. NaCl. Purification by silica gel gave 350 mg of the desired product. Yield: 26%.

Workup

  1. customflushed with H2 three times
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was then dissolved in EtOAc
  5. washwashed with 2N HCl, sat. NaHCO3, and sat. NaCl
  6. customPurification by silica gel

Sources & evidence

ORD record
ord-d9ab7bb3c00e4f1bacbda88f0ab4d4d9
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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