p-Anisoyl chloride → 1-(4-Methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2060231Notes

Reaction equation

HRID 2060231 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:19]([O:21][C:22]([CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:23])[CH3:20]>C1COCC1>[CH2:19]([O:21][C:22]([CH:24]1[CH2:28][CH2:27][N:26]([C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:25]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 12896002Ethyl pyrrolidine-3-carboxylate

Product 1

HCID 593221751-(4-Methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxy-benzoyl chloride (185 mL, 1.36 mol) and triethylamine (259 mL, 1.86 mol) were added to a stirred solution of pyrrolidine-3-carboxylic acid ethyl ester (177.5 g, 1.24 mol) (see Preparation 1) in THF (2500 mL) at 10° C. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with 10% citric acid aqueous solution (2000 mL) then ethyl acetate (2000 mL) was added. The organic layer was washed with saturated aqueous NaHCO3 (2000 mL) and water (2000 mL), dried over magnesium sulphate then concentrated under reduced pressure to afford the title compound as a brown oil (285.3 g, 83%).

Workup

  1. customThe reaction mixture was quenched with 10% citric acid aqueous solution (2000 mL)
  2. additionethyl acetate (2000 mL) was added
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (2000 mL) and water (2000 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-7807c4da78ec4579be22458df2ec0049
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

Loading…