Sodium Carbonate → HCID 22674982, compound

HRID 644020Notes

Reaction equation

HRID 644020 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 62576Benzyl bromoacetate

Product 1

HCID 22674982HCID 22674982, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl bromoacetate (500 mg, 2.18 mmol) was added to a mixture of pyrrolidine (171 mg, 2.40 mmol) and sodium carbonate (254 mg, 2.40 mmol) in tetrahydrofuran (7 ml). The mixture was stirred at room temperature for 18 h, then concentrated in vacuo. The residue was mixed with water (200 ml) and extracted with dichloromethane (3×100 ml). The organic layers were combined, dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography eluting with 0-10% (v/v) methanol in dichloromethane afforded pyrrolidin-1-yl acetic acid benzyl ester (230 mg, 1.05 mmol).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was mixed with water (200 ml)
  3. extractionextracted with dichloromethane (3×100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography
  7. washeluting with 0-10% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-9457b15352db4193b05d1154af06b8b0
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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