Pyrrolidine → HCID 67165963, compound

HRID 553249Notes

Reaction equation

HRID 553249 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([O:8][C:9]([C:11]1[O:12][C:13](CCl)=[CH:14][CH:15]=1)=[O:10])[CH3:7].[CH3:18]N(C)C(=O)C>>[CH2:6]([O:8][C:9]([C:11]1[O:12][C:13]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:14][C:15]=1[CH3:18])=[O:10])[CH3:7]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 31374DimethylacetamideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 67165963HCID 67165963, compoundYield 67%

Procedure

Pyrrolidine (0.75 g, 10.6 mmol) was added to an N,N-dimethylacetamide (15 ml) solution of 5-chloromethylfuran-2-carboxylic acid ethyl ester (1.0 g, 5.3 mmol), and stirred at room temperature for 24 hours. The solvent was evaporated, and the residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2) to afford 5-pyrrolidine-1-yl-methyl-furan-2-carboxylic acid ethyl ester (793 mg, 67%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-498c016002124dd981ff64347624918c
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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