Benzaldehyde → N-Benzylglycine ethyl ester

HRID 1456645Notes

Reaction equation

HRID 1456645 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:10]([O:12][C:13](=[O:16])[CH2:14][NH2:15])[CH3:11].CC([O-])=O.[Na+].C([BH3-])#N.[Na+]>CCO>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][NH:15][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:11]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 517045Sodium AcetateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 80908N-Benzylglycine ethyl esterYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzaldehyde (14.0 g, 0.132 mol) in absolute EtOH (500 mL) was added glycine ethyl ester hydrochloride (37.0 g, 0.256 mol), NaOAc (32.5 g, 0.396 mol) and sodium cyanoborohydride (9.8 g, 0.158 mol), and the resulting mixture heated to reflux. After 1 hr at reflux, the reaction was cooled and concentrated in vacuo. The residue was taken up into 1N NaOH and EtOAc. The layers were separated and the organic phase was washed with 1N NaOH, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was taken up into EtOAc (150 mL) and treated with gaseous HCl. The resulting solid was collected, washed with Et2O and dried to provide 23.4 g of compound 701 as the HCl salt. ##STR80##

Workup

  1. temperaturethe resulting mixture heated to reflux
  2. temperatureAfter 1 hr at reflux
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. customThe layers were separated
  6. washthe organic phase was washed with 1N NaOH, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. additiontreated with gaseous HCl
  11. customThe resulting solid was collected
  12. washwashed with Et2O
  13. customdried

Sources & evidence

ORD record
ord-1f6ae2e4e52046818072ff7bd3ae834b
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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