Methyl iodide → 1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

HRID 1034622Notes

Reaction equation

HRID 1034622 reaction equation
[CH3:1][C:2]1([C:17]([O-:19])=[O:18])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 602052331-Benzyl 3-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 602052351-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate (3.45 g, 13.1 mmol) in THF (20 mL) was added lithium bis(trimethylsilyl)amide (16.4 mL, 16.4 mmol) in THF at −78° C., and the reaction was stirred at this temperature for 20 minutes. MeI (1.10 mL, 17.7 mmol) was added, and the reaction was warmed to room temperature. After 2 hours at room temperature, the mixture was poured onto saturated ammonium chloride (20 mL) and extracted with ether, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (hexane:ethyl acetate 4:1) to give 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 75% yield) as an oil.

Workup

  1. waitAfter 2 hours at room temperature
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by chromatography (hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-f6728f3e2f8a494d95f688bc2b76d16f
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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