Water → HCID 23139175, compound

HRID 1171680Notes

Reaction equation

HRID 1171680 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[CH:11]=[CH:10][C:9](/[CH:12]=[C:13]3\[CH2:14][N:15]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:17][C:18]\3=[O:19])=[N:8]2)[N:3]=[CH:2]1.[BH4-].[Na+].O.C(OCC)(=O)C>CO>[S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[CH:11]=[CH:10][C:9](/[CH:12]=[C:13]3\[CH2:14][N:15]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:17][CH:18]\3[OH:19])=[N:8]2)[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 23138955HCID 23138955, compound

Product 1

HCID 23139175HCID 23139175, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-3-({1-[(1,3-thiazol-4-yl)methyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (2.48 g) in methanol (25 ml) was added sodium borohydride (0.09 g) at room temperature. After being stirred at the same temperature for 0.5 hour, water and ethyl acetate were added and the product was extracted. The separated organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave (E)-3-({1-[(1,3-thiazol-4-yl)methyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (ca. 2.5 g) as a crude pale yellow amorphous solid.

Workup

  1. extractionthe product was extracted
  2. washThe separated organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f5a2ebdf722440669a50170bba53af06
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…