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

HRID 751255Notes

Reaction equation

HRID 751255 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 (Preparation 1, Part A; 154 g, 0.66 mol), then 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-2f0d386772274e439ca81de782212621
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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