Water → 2-Methyl-2-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-ylmethyl]-malonic Acid Dimethyl Ester

HRID 479035

Reaction equation

HRID 479035 reaction equation
[CH3:1][CH:2]([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].I[CH2:14][C@@H:15]1[CH2:19][N:18]([C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:17](=[O:28])[CH2:16]1.O>CS(C)=O>[CH3:6][O:5][C:3](=[O:4])[C:2]([CH3:1])([CH2:14][C@H:15]1[CH2:16][C:17](=[O:28])[N:18]([C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[CH2:19]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69104Dimethyl methylmalonateHCID 10830178(S)-4-Iodomethyl-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

Product 1

HCID 590940412-Methyl-2-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-ylmethyl]-malonic Acid Dimethyl EsterYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To dimethyl methylmalonate (1.06 g, 7.29 mmol) in DMSO (7 mL) at room temperature was added NaH (291 mg of a 60% dispersion in oil). After the effervescence had ceased the lactam 85 (2 g, 7.29 mol) in DMSO (5 mL) was added. After 1 hour water was added and the aqueous solution extracted with ether. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/acetone) of the residue gave the product as an oil (1.7 g, 81%). MS m/z 348 (M+H, 100%).

Workup

  1. additionwas added
  2. extractionthe aqueous solution extracted with ether
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-44852ffcde6842a1ab8ae662b293886d
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Linked notes

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