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 1727161Notes

Reaction equation

HRID 1727161 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

To benzonitrile 21 (1.7 g 3.8 mmol) in EtOH/EtOAc was added 200 mg of Pd—C and flushed with H2 three times. The mixture was stirred under H2 at r.t. for 72 h. The mixture was filtered through celite and the filtrate was concentrated. Extraction of the filtrate with EtOAc and washing with 2N HCl, sat. NaHCO3, sat. NaCl, followed by purification with 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. concentrationthe filtrate was concentrated
  4. extractionExtraction of the filtrate with EtOAc
  5. washwashing with 2N HCl, sat. NaHCO3, sat. NaCl
  6. customfollowed by purification with silica gel

Sources & evidence

ORD record
ord-8dfa1a6784584a7e8123abf4681d199b
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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