Water → 1-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate

HRID 2203823Notes

Reaction equation

HRID 2203823 reaction equation
[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[NH:13]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1.CCOCC>[N:13]1([C:1]([O:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:10])[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 19261352Methyl pyrrolidine-3-carboxylate hydrochloride

Product 1

HCID 113460671-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylateYield 54.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl carbonochloridate (3.57 mL, 25.36 mmol) at 0° C. was added to methyl pyrrolidine-3-carboxylate hydrochloride (4.00 g, 24.15 mmol) and K2CO3 (6.68 g, 48.3 mmol) in THF:water (100 mL, 1:1). The reaction mixture was stirred at room temperature for 2 hours. Ether (50 mL) was added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give 1-benzyl 3-methyl pyrrolidine-1,3-dicarboxylate (3.45 g, 54% yield) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by chromatography (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-4d26ceb414e34589a9d46b5be5eab51e
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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