Sodium borohydride → N-((4-Methoxyphenyl)methyl)glycine methyl ester

HRID 2172064Notes

Reaction equation

HRID 2172064 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:17]=[CH:16][C:8](/[CH:9]=[N:10]/[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1>CO.C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178501580HCID 178501580, compound

Product 1

HCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (438 mg, 1.2 mmol) was added to a solution of (E)-methyl 2-(4-methoxybenzylideneamino)acetate (2.0 g, 9.6 mmol) in a mixture of methanol (22 mL) and THF (11 mL) at 0° C. The reaction mixture was stirred 1 hour at room temperature then partitioned between a solution of saturated ammonium chloride (20 mL) and ethyl acetate (30 mL). The aqueous phase was separated and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated to dryness. The title compound was obtained as a white oil (1.7 g, 85%).

Workup

  1. customthen partitioned between a solution of saturated ammonium chloride (20 mL) and ethyl acetate (30 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e0e0611ae986426db5e8fa04cbaf71ef
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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