Pyridine → 3-(2-Oxo-pyrrolidin-1-ylimino)-3-pyridin-2-yl-propionic acid ethyl ester

HRID 751259Notes

Reaction equation

HRID 751259 reaction equation
Cl.[NH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH2:9]([O:11][C:12](=[O:22])[CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:10].N1C=CC=CC=1>O>[CH2:9]([O:11][C:12](=[O:22])[CH2:13][C:14](=[N:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2736461Ethyl 3-oxo-3-(pyridin-2-yl)propanoateHCID 219928451-Aminopyrrolidin-2-one hydrochloride

Product 1

HCID 597100323-(2-Oxo-pyrrolidin-1-ylimino)-3-pyridin-2-yl-propionic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Place 1-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9(2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (200 g, 1.04 mol) then pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (500 mL), and extract with toluene (2×500 mL). Combine the organic layers, dry (sodium sulfate), filter and concentrate in vacuo to yield the subtitled compound as a dark oil (280 g, 98%). MS ES+ m/e 276 (M+1).

Workup

  1. custom155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet
  2. extractionextract with toluene (2×500 mL)
  3. dry with materialCombine the organic layers, dry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8a3daa83c0ab486baf0bf8b1a75c611f
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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