Ammonium Acetate → HCID 58353584, compound

HRID 1808722Notes

Reaction equation

HRID 1808722 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1.C([O-])(=O)C.[NH4+].[BH4-].[Na+]>CO>[OH:1][CH:2]([CH3:15])[CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 4311764Sodium borohydrideHCID 20134204Ethyl 4-(2-oxopropyl)benzoate

Product 1

HCID 58353584HCID 58353584, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(2-oxopropyl)benzoate (2.25 g, 10.9 mmol, 1 eq) and ammonium acetate (8.40 g, 109 mmol, 9.97 eq) were dissolved in MeOH (45 mL). While stirring at room temperature, sodium borohydride (684 mg, 18.1 mmol, 1.65 eq) was added. The resulting reaction mixture was stirred overnight at room temperature. The reaction was concentrated and partitioned between CH2Cl2 and 1M NaOH (aq.). The organic layer was removed and saved and the aqueous layer was extracted with CH2Cl2. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a residue which was purified via silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes, SiO2) to afford ethyl 4-(2-hydroxypropyl)benzoate (1.18 g, 52%). The same silica gel column was then subjected to a second set of chromatography conditions (gradient elution, 0% to 80% MeOH in EtOAc) to afford racemic ethyl 4-(2-aminopropyl)benzoate (610 mg, 27%).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight at room temperature
  3. concentrationThe reaction was concentrated
  4. custompartitioned between CH2Cl2 and 1M NaOH (aq.)
  5. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. washwashed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto afford a residue which
  12. customwas purified via silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes, SiO2)

Sources & evidence

ORD record
ord-52a22f1bd3af4fdba255ac2d44d47977
Source dataset
uspto-grants-2013_01
Patent number
US08361959B2

Reaction notes

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