Ethyl Acetate → HCID 66839348, compound

HRID 546660Notes

Reaction equation

HRID 546660 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]2[N:39]=[C:22]3[CH:23]([C:27]4[CH:32]=[CH:31][C:30]([C:33](=[O:38])[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:29][CH:28]=4)[CH2:24][CH2:25][CH2:26][N:21]3[N:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1.C(OCC)(=O)C>CO.[Cl-].[Na+].O>[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]2[N:39]=[C:22]3[CH:23]([C:27]4[CH:28]=[CH:29][C:30]([CH:33]([OH:38])[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:31][CH:32]=4)[CH2:24][CH2:25][CH2:26][N:21]3[N:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 66839269HCID 66839269, compound

Product 1

HCID 66839348HCID 66839348, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium tetrahydroborate (0.166 mg) was added to a solution of (−)-1-{4-{2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-yl}phenyl}pentan-1-one obtained in Example 3 (2 mg) in methanol (0.5 mL), and the reaction solution was stirred in a nitrogen atmosphere at room temperature for one hour. Brine and ethyl acetate were added to the reaction solution and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1) to obtain 1.19 mg of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-8c16c7e77ab5475fbb55d3718c960fe4
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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