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

HRID 2203824Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12]1.[CH3:30]I.[Cl-].[NH4+]>C1COCC1>[CH3:30][C:13]1([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:15][N:11]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium bis(trimethylsilyl)amide (16.4 mL, 16.4 mmol) was added to 1-benzyl 3-methyl pyrrolidine-1,3-dicarboxylate (3.45 g, 13.1 mmol) in THF (20 mL) at −78° C., and the reaction was stirred at −78° C. 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), 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

temperaturethe reaction was warmed to room temperature
waitAfter 2 hours at room temperature
extractionextracted with ether
washwashed with brine
dry with materialdried over sodium sulfate
customAfter removal of the solvent
customthe residue was purified by chromatography (hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-c310051d59624484aad50a43461e6073
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365568B2

Reaction notes

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