Ammonia → (R)-2-benzyl-4-hydroxybutyramide

HRID 1416875Notes

Reaction equation

HRID 1416875 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:14].ClCCl.CO>C(O)C>[CH2:1]([C@H:8]([CH2:13][CH2:12][OH:11])[C:9]([NH2:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11355800(R)-2-benzylbutyrolactoneHCID 21226129Dichloromethane methanol

Product 1

HCID 53683602(R)-2-benzyl-4-hydroxybutyramideYield 63.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-2-benzylbutyrolactone (1 gram) was dissolved in 5 ml of absolute ethanol, followed by the addition of 0.5 gram of gaseous ammonia. The solution was kept in a stoppered flask, and the progress of the reaction was followed by thin layer chromatography (eluent dichloromethane/methanol 20:1). After the reaction was judged complete, the ethanol was evaporated and the resulting residue redissolved in ethyl acetate. Ammonia was removed by extraction with 1% HCl, and the ethyl acetate solution was dried over MgSO4, filtered, and rotary evaporated to leave 0.7 grams of (R)-2-benzyl-4-hydroxybutyramide.

Workup

  1. customThe solution was kept in a stoppered flask
  2. customthe ethanol was evaporated
  3. dissolutionthe resulting residue redissolved in ethyl acetate
  4. customAmmonia was removed by extraction with 1% HCl
  5. dry with materialthe ethyl acetate solution was dried over MgSO4
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-43059cfc8e174e81af2d4aa5890e9e91
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

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