Water → HCID 57429670, compound

HRID 889048Notes

Reaction equation

HRID 889048 reaction equation
C([O:3][C:4]([C:6]1[CH2:10][CH:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[O:8][N:7]=1)=O)C.[BH4-].[Na+].O>C1COCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH:9]2[O:8][N:7]=[C:6]([CH2:4][OH:3])[CH2:10]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57429669HCID 57429669, compound

Product 1

HCID 57429670HCID 57429670, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-Fluoro-benzyl)-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester (0.17 g, 0.677 mmol) in THF (10 ml), NaBH4 (0.051 g, 0.81 mmol) was added slowly at 0° C. The reaction mixture was stirred for 2 h at room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue obtained was purified by column chromatography to obtain [5-(4-Fluoro-benzyl)-4,5-dihydro-isoxazol-3-yl]-methanol (140 mg, 100%) as an yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-622f49e2a3164720b994e9fbeaca5d55
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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