HCID 10069989, compound → HCID 66884727, compound

HRID 1582215Notes

Reaction equation

HRID 1582215 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]1[CH2:16][CH2:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1

Participants

4

Reactant 1

HCID 10069989HCID 10069989, compound

Product 1

HCID 66884727HCID 66884727, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (6 mg, 10 wt %) was added to a solution of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (59 mg, 0.14 mmol) in methanol (2 mL). The reaction mixture was evacuated and refilled with hydrogen (3×) then stirred at rt under a balloon of hydrogen for 3.5 h. The reaction mixture was filtered through celite, washing with methanol (5 mL). The filtrate was concentrated in vacuo to afford 59 mg (99%) of (4-{(R)-2-[4-(3-Chlorophenyl)-3-oxo-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester.

Workup

  1. customThe reaction mixture was evacuated
  2. additionrefilled with hydrogen (3×)
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashing with methanol (5 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-50885df735fc4f60a066ea780252a0a5
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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