Triethylamine → HCID 57743085, compound

HRID 1896484Notes

Reaction equation

HRID 1896484 reaction equation
[NH2:1][CH2:2][CH:3]([CH2:10][CH2:11][CH3:12])[CH2:4][C:5]([O:7]CC)=O.[OH:13][CH2:14][C:15](=[CH2:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].CCN(CC)CC>CCO.C1COCC1>[OH:13][CH2:14][CH:15]([CH2:21][N:1]1[CH2:2][CH:3]([CH2:10][CH2:11][CH3:12])[CH2:4][C:5]1=[O:7])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl esterHCID 53629152HCID 53629152, compound

Product 1

HCID 57743085HCID 57743085, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a three neck flask, fitted with a reflux condenser, under argon, a solution of ethyl 3-(aminomethyl)hexanoate (11.8 g, 0.042 mol) in EtOH (50 ml) is added via a pump-syringe (5 ml/h) onto a solution of ethyl 2-(hydroxymethyl)acrylate x278 (5 g, 0.038 mol) and Et3N (8.03 ml) in THF (100 ml) at room temperature. After 6 h, the reaction mixture is filtered on celite, washed with saturated NaHCO3 and the aqueous layer is extracted with CH2Cl2 (2×150 ml), dried with MgSO4, filtered and concentrated in vacuo. The crude reaction mixture is purified by chromatography on silicagel (CH2Cl2/MTBE/MeOH 50/49/1), to afford 3.7 g of ethyl 3-hydroxy-2-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]propanoate c279.

Workup

  1. customIn a three neck flask, fitted with a reflux condenser, under argon
  2. filtrationthe reaction mixture is filtered on celite
  3. washwashed with saturated NaHCO3
  4. extractionthe aqueous layer is extracted with CH2Cl2 (2×150 ml)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude reaction mixture
  9. customis purified by chromatography on silicagel (CH2Cl2/MTBE/MeOH 50/49/1)

Sources & evidence

ORD record
ord-e56c1b98ab1c4948be3a699cf1200411
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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