Trifluoroacetic acid → (5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-one

HRID 22965

Reaction equation

HRID 22965 reaction equation
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9]([O:11][CH2:12][CH3:13])=[CH2:10].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:9]([O:11][CH:12]([O:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)[CH3:13])[CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8023Ethyl vinyl etherHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 12137689(5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-oneYield 102%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (5R)-5-(hydroxymethyl)pyrrolidin-2-one (Aldrich, 8.86 g, 77 mmol) in 70 mL of chloroform at room temperature under an argon atmosphere was added ethyl vinyl ether (10.4 mL, 108 mmol) and catalytic anhydrous trifluoroacetic acid (0.2 mL). After stirring for 3 hours, the reaction was partitioned between methylene chloride (150 mL) and aqueous sodium bicarbonate solution (150 mL) and the phases were separated. The organic phase was dried (K2CO3) and filtered. The filtrate was evaporated under reduced pressure to give 14.7 g of the (5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-one.

Workup

  1. customthe reaction was partitioned between methylene chloride (150 mL) and aqueous sodium bicarbonate solution (150 mL)
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried (K2CO3)
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a33fe86201f24b20b09fad2d95879b46
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Linked notes

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