Sodium borohydride → HCID 178520876, compound

HRID 1935727Notes

Reaction equation

HRID 1935727 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:19](=[O:26])[CH2:20][C:21](OCC)=[O:22])[C:5]2[NH:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:18]=1.[BH4-].[Na+]>C(O)C>[OH:26][CH:19]([C:4]1[C:5]2[NH:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:18]=[C:2]([OH:1])[CH:3]=1)[CH2:20][CH2:21][OH:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178472184HCID 178472184, compound

Product 1

HCID 178520876HCID 178520876, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of Ethyl 3-(6-hydroxy-2-(2-phenylethyl)benzimidazol-4-yl)-3-oxopropanoate (500 mg) obtained in Inventive Example 42 in anhydrous ethanol (10 mL), while cooling in an ice bath, was added sodium borohydride (81 mg), and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ice water (20 mL) and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was crystallized from ether to obtain the desired compound as colorless crystal (424 mg).

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was crystallized from ether

Sources & evidence

ORD record
ord-24922fee74a04d63adc872da171c25da
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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