Water → HCID 19028730, compound

HRID 2256338Notes

Reaction equation

HRID 2256338 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][C:5](OCC)=[O:6])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:2][CH2:1][C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:4][CH2:5][OH:6]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19028748HCID 19028748, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 19028730HCID 19028730, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-cyano-3,3-diphenylpropionate (reference compound 2-1) (1.2 g) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (0.44 g) portionwise with ice-cooling and stirring. After completion of dropwise addition, the mixture was heated and stirred at 60° C. for 3 hours. The reaction mixture was then cooled with ice again, and water (1 ml), 15% aqueous sodium hydroxide solution (3 ml) and water (1 ml) were added in the order mentioned. The resulting precipitate was filtered off and the filtrate was extracted using ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was washed with ethyl acetate to provide the title compound (0.82 g) as colorless powder.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. temperaturethe mixture was heated
  4. stirringstirred at 60° C. for 3 hours
  5. temperatureThe reaction mixture was then cooled with ice again
  6. filtrationThe resulting precipitate was filtered off
  7. extractionthe filtrate was extracted
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated to dryness
  12. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-c38c04ad98a14ffb86ad77e43fbcf876
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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