Pyridine → 3-(6-Methyl-pyridin-2-yl)-3-(2-oxo-pyrrolidin-1-ylimino)-propionic Acid Ethyl Ester

HRID 2221144Notes

Reaction equation

HRID 2221144 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:23])[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1)=O)[CH3:10].N1C=CC=CC=1>O>[CH2:9]([O:11][C:12](=[O:23])[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1)=[N:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 219928451-Aminopyrrolidin-2-one hydrochlorideHCID 59710028Ethyl 3-(6-methylpyridin-2-yl)-3-oxopropanoate

Product 1

HCID 597100333-(6-Methyl-pyridin-2-yl)-3-(2-oxo-pyrrolidin-1-ylimino)-propionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 1-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem. 1969, 9(2), 58; 99.4 g, 0.73 mol) to a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-[6-methyl-(pyridin-2-yl)]-3-oxo-propionic acid ethyl ester (154 g, 0.66 mol), and pyridine (280 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (200 mL) and extract with toluene (2×250 mL). Combine the organic layers, filter, and concentrate in vacuo to yield the subtitled product (201 g) as a dark oil. MS ES+ m/e 290 (M+1).

Workup

  1. custom99.4 g, 0.73 mol) to a 3 L flask equipped with mechanical stirrer and nitrogen inlet
  2. extractionextract with toluene (2×250 mL)
  3. filtrationCombine the organic layers, filter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-c12874eff9284e05a25ef5a8a9f8189a
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

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