Water → HCID 15411702, compound

HRID 1935721Notes

Reaction equation

HRID 1935721 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[N:4]=[C:3]1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].O>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[N:4]=[C:3]1[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 15411701HCID 15411701, compound

Product 1

HCID 15411702HCID 15411702, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 3-(1-methyl-2-(2-phenylethyl)benzimidazol-4-yl)-3-oxopropanoate (0.80 g) obtained in Inventive Example 10 in anhydrous methanol (16 mL), was added sodium borohydride in small portions which was cooled in an ice bath. After stirring for 20 minutes at room temperature, the reaction solution was poured into water and concentrated under a reduced pressure. The thus obtained residue was extracted with ethyl acetate, and the organic layer was washed with water and brine in that order. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound as white crystal (0.39 g).

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationconcentrated under a reduced pressure
  3. extractionThe thus obtained residue was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine in that order
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-efa1706a50fc440884434788071a507c
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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