Sodium borohydride → HCID 54516649, compound

HRID 549419Notes

Reaction equation

HRID 549419 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-85e248d125d44de0bc5d36dfdd48feed
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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