Sodium borohydride → HCID 22988405, compound

HRID 987132Notes

Reaction equation

HRID 987132 reaction equation
[C:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[C:4](OCC)=[O:5])#[N:2].[BH4-].[Na+]>CO>[C:1]([CH:3]([CH2:4][OH:5])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22988457HCID 22988457, compound

Product 1

HCID 22988405HCID 22988405, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-cyano-3-(4-{2-[4-(isobutyrylamino)phenyl]ethoxy}phenyl)propanoate (0.5 g, 1.22 mmol) was dissolved in methanol (10 ml). Sodium borohydride (0.24 g, 6.34 mmol) was added carefully. The mixture was stirred at room temperature for 4 hours and then evaporated in vacuum to dry. Ethyl acetate and water were added into the residue. After separation, the organic phase was washed with 0.3 M hydrochloric acid, water and brine. The solvent was evaporated in vacuum. Column chromatography of the residue on silica gel using ethyl acetate/heptane as eluant gave 0.33 g desired product, yield 74%.

Workup

  1. customevaporated in vacuum
  2. customto dry
  3. additionEthyl acetate and water were added into the residue
  4. customAfter separation
  5. washthe organic phase was washed with 0.3 M hydrochloric acid, water and brine
  6. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-8f7c9dd989574b0e9a02989c7b179b38
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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