Methanol → Methyl 2-(phenethylamino)acetate

HRID 1067078Notes

Reaction equation

HRID 1067078 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].CO.[C:10]1([CH2:16][CH:17]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:17]([NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])[CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 998PhenylacetaldehydeHCID 122755Glycine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22991956Methyl 2-(phenethylamino)acetateYield 33.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A cold solution (0° C.) of glycine methyl ester hydrochloride (1.0 g, 8 mmol), methanol (25 mL), glacial acetic acid (0.8 mmol, and phenylacetaldehyde (0.481 g, 4 mmol) was treated with sodium triacetoxyborohydride (1.7 g, 8 mmol) in two portions. The reaction mixture was maintained at 0° C. for 1.5 hr, and then quenched with saturated sodium bicarbonate (15 mL). The solution was extracted with ethyl acetate. The organic phase was collected, dried over anhydrous sodium sulfate, and adsorbed onto silica gel (100 mg) and applied to a column prepacked with silica gel. The column was eluted with CH2Cl2/MeOH (97:3, v:v) to afford titled compound (258 mg).

Workup

  1. customquenched with saturated sodium bicarbonate (15 mL)
  2. extractionThe solution was extracted with ethyl acetate
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. washThe column was eluted with CH2Cl2/MeOH (97:3, v:v)

Sources & evidence

ORD record
ord-dfb5b0aa1c8348a3bf90a2029924398e
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

Loading…