Iodoethane → 4-(R)-[1-[N-(tert-butoxycarbonyl)-N-(ethyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidin-2-one

HRID 600901Notes

Reaction equation

HRID 600901 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C@H:12]2[CH2:16][N:15]([C@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[C:14](=[O:25])[CH2:13]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28](I)[CH3:29].[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:9]1([C@H:12]2[CH2:16][N:15]([C@H:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:18])[C:14](=[O:25])[CH2:13]2)[CH2:11][CH2:10]1)[CH2:28][CH3:29])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672716654-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidin-2-one

Product 1

HCID 672718654-(R)-[1-[N-(tert-butoxycarbonyl)-N-(ethyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidin-2-one (4.16 g, 12.1 mmol) was dissolved in dimethylformamide (50 ml). Under a nitrogen atmosphere and at room temperature, 60% oily sodium hydride (580 mg, 14.5 mmol) was added thereto and stirred for 10 minutes, and then ethyl iodide (4.87 ml, 60.5 mmol) was added dropwise. After completion of dripping, the reaction suspension was stirred at room temperature for 15 hours. After adding a saturated aqueous ammonium chloride solution (150 ml) to the reaction suspension while stirring and cooling with ice, extraction with ethyl acetate (150 ml×2) was performed. The combined organic layer was then washed with water (150 ml×2) and saturated saline solution (150 ml) in that order, and then dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the residue obtained was applied to a silica gel chromatography, and 4.56 g (quantitative) of the title compound was obtained in the form of a colorless oily substance from an n-hexane:ethyl acetate=1:2 eluate.

Workup

  1. stirringthe reaction suspension was stirred at room temperature for 15 hours
  2. stirringwhile stirring
  3. washThe combined organic layer was then washed with water (150 ml×2) and saturated saline solution (150 ml) in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtering
  6. concentrationthe filtrate was concentrated under a reduced pressure
  7. customthe residue obtained

Sources & evidence

ORD record
ord-3fd0f3708c8a4361b0db727adb072eeb
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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