HCID 68462203, compound → HCID 57563708, compound

HRID 1726329Notes

Reaction equation

HRID 1726329 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:8][C:7]=1[C:18](O)=[O:19]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:8][C:7]=1[CH2:18][OH:19]

Participants

3

Reactant 1

HCID 68462203HCID 68462203, compound

Product 1

HCID 57563708HCID 57563708, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3-(4-(pyrazol-1-ylmethyl)-2-carboxyphenyl)propanoic acid methyl ester (600 mg) in anhydrous THF (8.0 ml) was added dropwise a solution of borane-tetrahydrofuran complex in THF (3.2 ml) at 0° C. and the mixture was stirred at room temperature for 2.5 hours. To the mixture was added a solution of borane-tetrahyrofuran complex in THF (3.5 ml) and the mixture was stirred for 1 hour. To the reaction solution was added ice and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give the title compound (420 mg) having the following physical data.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. additionTo the reaction solution was added ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-923325d46a974de8ba221f04e278c3b6
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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