Iodoethane → HCID 117840378, compound

HRID 714804Notes

Reaction equation

HRID 714804 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH:12]([CH3:13])[CH2:11][CH2:10][C:9]2=[O:14])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH2:28][CH3:29].[Cl-].[NH4+]>O1CCCC1>[CH2:28]([CH:10]1[CH2:11][CH:12]([CH3:13])[N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:14])[CH3:29]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 102107471HCID 102107471, compound

Product 1

HCID 117840378HCID 117840378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methoxybenzyl)-5-methylpyrrolidin-2-one (3.0 g) obtained in Step A in tetrahydrofuran (25 mL) was added sodium bis(trimethylsilyl)amide (1.9M tetrahydrofuran solution, 11 mL) at −78° C. under nitrogen atmosphere, and the mixture was stirred at the same temperature for 1 hr. Iodoethane (2.2 mL) was added thereto, and the mixture was stirred overnight while it was allowed to be warmed. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.5 g).

Workup

  1. stirringthe mixture was stirred overnight while it
  2. temperatureto be warmed
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fbc8bd56167d4496b78fa91e7f039f81
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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