4-Methylmorpholine → 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione

HRID 2426354Notes

Reaction equation

HRID 2426354 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[O:6][CH2:5][CH2:4][O:3]1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][C:2]1([CH2:7][CH2:8][C:9]([O:11][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])=[O:10])[O:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109317243-(2-methyl-1,3-dioxolan-2-yl)propanoic Acid

Product 1

HCID 860518291-{[3-(2-Methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dioneYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-methyl-1,3-dioxolan-2-yl)propanoic acid (8.95 g, 55.9 mmol) in dichloromethane (111 mL) was cooled to approximately 0° C. N-hydroxysuccinimide (7.10 g, 61.5 mmol), 4-methylmorpholine (6.22 g, 61.5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.8 g, 61.5 mmol) were sequentially added with stirring. The reaction was then allowed to warm to room temperature, stirred for 17 hours, and partitioned between dichloromethane (150 mL) and water (50 mL). The organic layer was separated; sequentially washed with water (50 mL), saturated aqueous sodium bicarbonate (2×50 μL), and brine (50 mL); dried over sodium sulfate; filtered; and concentrated under reduced pressure to provide 13 g of 1-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione as a white solid.

Workup

  1. stirringstirred for 17 hours
  2. custompartitioned between dichloromethane (150 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. washsequentially washed with water (50 mL), saturated aqueous sodium bicarbonate (2×50 μL), and brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationand concentrated under reduced pressure

Sources & evidence

ORD record
ord-e91da395f1de4bc1bec49f2bdbaac999
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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