Sodium borohydride → HCID 86635467, compound

HRID 2261792Notes

Reaction equation

HRID 2261792 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:18]=[CH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[CH:10][C:9]=1[CH3:32])[CH3:7])C.[BH4-].[Na+]>C1COCC1.CO>[Cl:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([Cl:30])[C:24]=1[N:17]1[C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH:6]([CH3:7])[CH2:5][CH2:4][OH:3])=[C:9]([CH3:32])[CH:10]=2)=[C:20]([CH:21]([CH3:23])[CH3:22])[CH:19]=[N:18]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86635465HCID 86635465, compound

Product 1

HCID 86635467HCID 86635467, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(+/−)-3-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-butyric acid ethyl ester (0.581 g, 1.19 mmol) is dissolved in THF (15 mL) and methyl alcohol (3 mL). Sodium borohydride is added portionwise until an excess has been added. After stirring at room temperature for 3 days, the reaction is quenched with water followed by 1N HCl. The resulting mixture is extracted two times with ethyl acetate. The organic layers are combined, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with 5-10% ethyl acetate:toluene to give the title compound. 1H NMR (CDCl3) δ 1.134 (d, 3H), 1.262 (d, 6H), 1.456 (s, 2H), 1.764 (m, 2H), 2.223 (s, 3H), 2.939-3.039 (m, 2H), 3.476-3.539 (m, 2H), 4.747 (s, 2H), 6.516 (d, 1H), 6.559 (dd, 1H), 6.99 (d, 1H), 7.263 (t, 1H), 7.372 (d, 2H), 7.663 (s, 1H)

Workup

  1. additionan excess has been added
  2. customthe reaction is quenched with water
  3. extractionThe resulting mixture is extracted two times with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified via flash chromatography
  9. washeluting with 5-10% ethyl acetate

Sources & evidence

ORD record
ord-1286b168db7242a793c3bfabed6bff1c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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