Ethyl 4-(2-aminoethyl)benzoate → Ethyl acetate hexane

HRID 2184343Notes

Reaction equation

HRID 2184343 reaction equation
N[CH2:2][CH2:3][C:4]1C=C[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1>C1COCC1>[C:8]([O:10][CH2:11][CH3:12])(=[O:9])[CH3:7].[CH3:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 1

HCID 12945884Ethyl 4-(2-aminoethyl)benzoate

Product 1

HCID 21226206Ethyl acetate hexaneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.98 g (9.59 mmol) (S)—O-Benzyl-dihydro-5-hydroxymethyl-2(3H)furanone and 3.14 g (16.25 mmol) ethyl p-aminoethylbenzoate were dissolved in 50 mL THF and stirred at 50° C. for 20 hours. Reaction was concentrated and crude residue purified via chromatography, eluting with 50% ethyl acetate/hexane yielding 2.24 g (5.61 mmol, 58% yield) N′-[2-(4-carboethoxyphenyl)ethyl]-5-benzyloxy-4-hydroxypentanamide as a white solid. Step 3

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customcrude residue purified via chromatography

Sources & evidence

ORD record
ord-13b1f948255f484886d5eb7f44ec37ba
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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