Sodium borohydride → HCID 54516649, compound

HRID 1802792Notes

Reaction equation

HRID 1802792 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6](=[O:18])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]([CH3:11])[C:9]=1[CH3:10].[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[OH:2][CH2:3][CH2:4][C:5]1[C:6](=[O:18])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]([CH3:11])[C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57899237HCID 57899237, compound

Product 1

HCID 54516649HCID 54516649, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) solution of (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (122 mg, 0.479 mmol) in ethanol (5 mL) were added CaCl2.2H2O (68.9 mg, 0.469 mmol) and sodium borohydride (37.4 mg, 0.937 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 4-(2-hydroxy-ethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (33.7 mg, 31% yield). LCMS 233.3 (M+1).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b80570f8be374e219527a1d3156aba35
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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