Water → Methyl 3-methoxy-4-(pyrrolidin-1-ylmethyl)benzoate

HRID 650019Notes

Reaction equation

HRID 650019 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O>C1COCC1>[CH3:14][O:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH2:2][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 10824510Methyl 3-methoxy-4-(pyrrolidin-1-ylmethyl)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-bromomethyl-3-methoxybenzoate (1.0 g; 3.9 mmol) (Part D) was dissolved in THF (10 mL) and pyrrolidine (1.3 mL; 15.4 mmol) was added at room temperature. The mixture was stirred overnight at room temperature, then poured into 50 mL of water. Extraction was carried out with EtOAc (4×25 mL). The combined organics were washed with brine and dried by passage through sodium sulfate. The title compound was isolated (0.92 g; 96% yield) by flash chromatography on silica gel eluting with EtOAc(100-95%)/Et3N(0-5%).

Workup

  1. extractionExtraction
  2. washThe combined organics were washed with brine
  3. dry with materialdried by passage through sodium sulfate

Sources & evidence

ORD record
ord-f88a7976c547414283df9ed5ed00079e
Source dataset
uspto-grants-2001_08
Patent number
US06271227B1

Reaction notes

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