4-Methoxybenzaldehyde → N-[(4-Methoxyphenyl)methyl]glycine ethyl ester

HRID 1362068Notes

Reaction equation

HRID 1362068 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[BH3-]C#N.[Na+].[CH:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>CO>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:3]

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 11736212N-[(4-Methoxyphenyl)methyl]glycine ethyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of glycine ethyl ester hydrochloride (10.0 g, 71.6 mmol) and NaBH3CN (5.00 g, 79.6 mmol) in MeOH (60 mL) was treated dropwise over 15 min with p-anisaldehyde (11.0 mL, 90.4 mmol). After stirring at room temperature overnight, the solvent was removed in vacuo. The residue was partitioned between CH2Cl2 (200 mL) and saturated aqueous NaHCO3 (300 mL). The aqueous layer was extracted with CH2Cl2 (2×200 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, hexanes/EtOAc, 90:10 to 50:50) gave the title compound (7.77 g, 49%) as a colorless liquid: MS (ESI) m/e 224 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 (200 mL) and saturated aqueous NaHCO3 (300 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×200 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customPurification by flash column chromatography (silica gel, hexanes/EtOAc, 90:10 to 50:50)

Sources & evidence

ORD record
ord-6d71abff6e2f47778083623e55d2f054
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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