2-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid monoethyl ester → 2-(2-Morpholin-4-yl-2-oxoethyl)-5-phenyl-pentanoic acid ethyl ester

HRID 1830144Notes

Reaction equation

HRID 1830144 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH2:18][C:19]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20])([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(O)=O)[CH3:2]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([CH2:18][C:19]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

3

Reactant 1

HCID 210256902-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid monoethyl ester

Product 1

HCID 210310262-(2-Morpholin-4-yl-2-oxoethyl)-5-phenyl-pentanoic acid ethyl esterYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A Solution of 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid monoethyl ester (809 mg, 2.14 mmol) in toluene (25 ml) was heated under reflux for 23 hours. The colorless solution was concentrated under reduced pressure, the residue was taken up in diethyl ether (50 ml), washed with saturated NaHCO3 and dried over MgSO4. The solvent was evaporated under reduced pressure to give 2-(2-morpholin-4-yl-2-oxoethyl)-5-phenyl-pentanoic acid ethyl ester as yellow oil (617 mg); 1H NMR (CDCl3) 7.37–7.1 (m, 5H), 4.2 (m, 2H), 3.8–3.4 (m, 8H), 3.0 (m, 1H), 2.75 (dd, J=15.9, 9.4 Hz, 1H), 2.65 (m, 2H), 2.35 (dd, J=15.9, 5.1 Hz, 1H), 1.8–1.55 (m, 4H), 1.29 (t, J=7.1 Hz, 3H). MS: 334 (MH+).

Workup

  1. temperatureunder reflux for 23 hours
  2. concentrationThe colorless solution was concentrated under reduced pressure
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f24eceb1b7024963b8fef5246a1f3148
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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