Methyl p-toluenesulfonate → HCID 71252638, compound

HRID 2411659Notes

Reaction equation

HRID 2411659 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C@@H:27]([CH2:28][OH:29])[CH2:26][CH2:25][C:24]4=[O:30])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].O1CCC[CH2:34]1.S(C1C=CC(C)=CC=1)(OC)(=O)=O>O>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[C@@H:27]([CH2:28][O:29][CH3:34])[CH2:26][CH2:25][C:24]4=[O:30])=[CH:21][CH:22]=3)=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 71253199HCID 71253199, compound

Product 1

HCID 71252638HCID 71252638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (R)-1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-hydroxymethylpyrrolidin-2-one (200 mg) described in Example 284 and sodium hydride (22 mg) was added tetrahydrofuran, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added methyl tosylate (74 μL), and the mixture was further stirred at room temperature for 2 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give (R)-1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-methoxymethylpyrrolidin-2-one. The obtained (R)-1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-methoxymethylpyrrolidin-2-one was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate was added, and the precipitate was collected by filtration to give the title compound (113 mg).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 days
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ba9b45e041034a75bb4d76f43b6f56cc
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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