Methyl iodide → 1-Methyl-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one

HRID 2175537Notes

Reaction equation

HRID 2175537 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([CH:13]3[NH:17][C:16](=[O:18])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.CI.[C:21]([O-])(O)=O.[Na+]>C1COCC1>[CH3:21][N:17]1[CH:13]([CH:10]2[CH2:9][CH2:8][C:7]3([O:3][CH2:4][CH2:5][O:6]3)[CH2:12][CH2:11]2)[CH2:14][CH2:15][C:16]1=[O:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68003854HCID 68003854, compound

Product 1

HCID 585628651-Methyl-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (27 mg, 1.07 mmol, 95%) in THF under argon was added 5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one (135 mg, 0.60 mmol, prepared in the Example 12 Step E). After stirring 1 hour at room temperature, Methyl iodide (0.07 mL, 1.12 mmol) was added dropwise and the reaction stirred at room temperature overnight. The reaction mixture was poured onto saturated NaHCO3 and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 0-100% ethyl acetate/DCM).

Workup

  1. customprepared in the Example 12 Step E)
  2. stirringthe reaction stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue purified by flash chromatography (silica gel, 0-100% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-45e09f18d26048f38dfa67758f5d6bd2
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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