Dichloromethane → HCID 178516483, compound

HRID 1171700Notes

Reaction equation

HRID 1171700 reaction equation
[BH4-].[Na+].[NH:3]1[CH:7]=[N:6][C:5](/[CH:8]=[C:9]2\[CH2:10][N:11]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:14]\2=[O:15])=[N:4]1.ClCCl>CO>[NH:3]1[CH:7]=[N:6][C:5](/[CH:8]=[C:9]2\[CH2:10][N:11]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:13][CH:14]\2[OH:15])=[N:4]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 178516481HCID 178516481, compound

Product 1

HCID 178516483HCID 178516483, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (131 mg) was added to a solution of (E)-3-[(1,2,4-triazol-3-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one (2.92 g) in a mixed solvent of dichloromethane (60 ml) and methanol (60 ml) at 0° C. After the mixture was stirred at room temperature for 30 minutes, the reaction was quenched by addition of a saturated aqueous ammonium chloride solution. Products were extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Solvents were removed under reduced pressure to afford crude (E)-3-[(1,2,4-triazol-3-yl)methylidene]-1-(triphenylmethyl)piperidin-4-ol. The crude product was dissolved in acetonitrile (60 ml) and methyl bromoacetate (920 μl) was added. After DBU (1.25 ml) was added thereto under cooling at 0° C., the mixture was stirred at 0° C. for 15 minutes. Water and ethyl acetate were added to the mixture and the layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent by evaporation under reduced pressure gave an approximately 1:3 mixture of the two title isomers (2.98 g, yield: 87%) as a pale yellow amorphous solid.

Workup

  1. customthe reaction was quenched by addition of a saturated aqueous ammonium chloride solution
  2. extractionProducts were extracted with ethyl acetate
  3. washthe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-3d1dd936d07a4f4bbd72f5c45226f1e4
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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