Pyrrolidine → Methyl 3-bromo-4-(pyrrolidin-1-ylmethyl)benzoate

HRID 1387069Notes

Reaction equation

HRID 1387069 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12]Br)[C:5]([O:7][CH3:8])=[O:6].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoate

Product 1

HCID 10803994Methyl 3-bromo-4-(pyrrolidin-1-ylmethyl)benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-bromo-4-bromomethylbenzoate (0.61 g; 2.0 mmol) (Part A) was dissolved in THF (10 mL) and pyrrolidine (0.66 mL; 7.9 mmol) was added at room temperature. The mixture was stirred overnight at room temperature, then poured into 80 mL of saturated aqueous aqueous sodium bicarbonate. Extraction was carried out with EtOAc (3×35 mL). The combined organics were washed with brine and dried by passage through sodium sulfate. The product was isolated as a colorless oil (0.46 g; 80% yield) by flash chromatography on silica gel eluting with EtOAc.

Workup

  1. extractionExtraction
  2. washThe combined organics were washed with brine
  3. dry with materialdried by passage through sodium sulfate
  4. customThe product was isolated as a colorless oil (0.46 g; 80% yield) by flash chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-e7535652fc5a45c9918634eabc8b1e79
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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