Tetrahydrofuran → HCID 69422978, compound

HRID 350074Notes

Reaction equation

HRID 350074 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19](/[CH:28]=[CH:29]/[C:30]([O:32]CC)=[O:31])=[CH:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.O1CCCC1>[C].[Pd].C(O)C>[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:19]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 69424087HCID 69424087, compound

Product 1

HCID 69422978HCID 69422978, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Catalytic hydrogenation of a mixture of ethyl(E)-3-[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]propenoate (1.32 g), 5% palladium-carbon (1.0 g), tetrahydrofuran (40 ml) and ethanol (40 ml) was conducted at ordinary temperature and ordinary pressure. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was dissolved in a mixed solution of tetrahydrofuran (10 ml) and ethanol (10 ml), then 1N aqueous sodium hydroxide solution (10 ml) was added to the solution, which was stirred at room temperature for 2 hours. The reaction mixture was poured into water, then neutralized with 1N hydrochloric acid (10 ml), which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The colorless crystals obtained were collected by filtration to yield 3-[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (900 mg, yield: 72%). This was recrystallized from acetone-ethyl acetate. Melting point: 110–111° C.

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in a mixed solution of tetrahydrofuran (10 ml) and ethanol (10 ml)
  4. addition1N aqueous sodium hydroxide solution (10 ml) was added to the solution, which
  5. additionThe reaction mixture was poured into water
  6. extractionwas extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe colorless crystals obtained
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d982165ed39d49dc923ea9a09f2dbf37
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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