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

HRID 1256631

Reaction equation

HRID 1256631 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]Br)[CH:10]=1.[Na]>O1CCCC1>[CH3:6][O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:10]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 5360545Sodium

Product 1

HCID 53429637Methyl 3-(pyrrolidin-1-ylmethyl)benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of pyrrolidine (7.3 mL, 87 mmol) in dry tetrahydrofuran (5 mL), a solution of 3-bromomethyl-benzoic acid methyl ester (2.0 g, 8.7 mmol) in 5 mL of dry tetrahydrofuran was added dropwise and the mixture stirred at room temperature for 4 hours. The reaction mixture was then poured into 100 mL of saturated aqueous solution of sodium hydrogenocarbonate, extracted with 100 mL of ethyl acetate, dried over sodium sulfate and evaporated to dryness affording the title compound as yellow oil (1.85 g).

Workup

  1. extractionextracted with 100 mL of ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-0ecfb111cdad46a7ac4837b209145c96
Source dataset
uspto-grants-2013_06
Patent number
US08461193B2

Linked notes

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