Pyrrolidine → Ethyl 2-phenyl-2-(pyrrolidin-1-yl)acetate

HRID 404629Notes

Reaction equation

HRID 404629 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC[N:16]([CH:20]([CH3:22])C)[CH:17]([CH3:19])C.N1CCCC1>C(#N)C>[C:8]1([CH:2]([N:16]2[CH2:17][CH2:19][CH2:22][CH2:20]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 3568733Ethyl 2-phenyl-2-(pyrrolidin-1-yl)acetateYield 109.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) was dissolved in acetonitrile (4.0 ml). DIPEA (0.26 ml, 1.48 mmol) and pyrrolidine (0.12 ml, 1.48 mmol) were sequentially added and the solution was stirred at room temperature for 1.5 hours. Acetonitrile was evaporated and the residue was purified by flash chromatography (petroleum ether/EtOAc=9/1) to obtain ethyl 2-phenyl-2-(pyrrolidin-1-yl)acetate (315 mg, quantitative yield) as a colorless oil.

Workup

  1. customAcetonitrile was evaporated
  2. customthe residue was purified by flash chromatography (petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record
ord-6042ede0df6a4d68b0a5cbaac566f561
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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