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

HRID 2203693Notes

Reaction equation

HRID 2203693 reaction equation
[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5][CH2:4][CH:3]([C:6]([O:8][CH3:9])=[O:7])[CH2:2]1.[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI.[Cl-].[NH4+]>C1COCC1>[CH3:20][C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:4][CH2:5][N:1]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 113460671-Benzyl 3-methyl pyrrolidine-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-methyl pyrrolidine-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-e581340aee0c45cda6f7426c70777e64
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

Loading…