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

HRID 2221148Notes

Reaction equation

HRID 2221148 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 (Preparation 3-A; 200 g, 1.04 mol) and 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 280 g (98%) of the subtitled compound as a dark oil. 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-71c2a20f2eeb4a50ad39f3c8d1e8cee5
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

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