Ethyl 2-((3-(benzyloxy)phenyl)(ethyl)amino)acetate → Ethyl 2-(ethyl(3-hydroxyphenyl)amino)acetate

HRID 709643Notes

Reaction equation

HRID 709643 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:15]([CH2:22][CH3:23])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:22]([N:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=1)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:23]

Participants

4

Reactant 1

HCID 117759917Ethyl 2-((3-(benzyloxy)phenyl)(ethyl)amino)acetate

Product 1

HCID 18915234Ethyl 2-(ethyl(3-hydroxyphenyl)amino)acetateYield 52.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-((3-(benzyloxy)phenyl)(ethyl)amino)acetate (960 mg) in methanol (30 mL) was added 10% palladium-activated carbon (300 mg) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 12 hr. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (360 mg) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3fb8a6bd6a8245ea9d12ca1bf2fa1bfb
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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