Trifluoroacetic acid → HCID 59075091, compound

HRID 2184337Notes

Reaction equation

HRID 2184337 reaction equation
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[C:5]([CH3:10])([CH3:9])[CH2:4]1.[CH:11]([O:13][CH2:14][CH3:15])=[CH2:12].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:11]([O:13][CH:14]([O:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[C:5]([CH3:10])([CH3:9])[CH2:4]1)[CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8023Ethyl vinyl etherHCID 59075103HCID 59075103, compound

Product 1

HCID 59075091HCID 59075091, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (R)-5-hydroxymethyl-3,3-dimethyl-pyrrolidin-2-one (4.0 g, 28 mmol), prepared as described in Tetrahedron 1998, 54 10295-10307, and ethyl vinyl ether (4 mL, 42 mmol) in chloroform (26 mL), was added a catalytic amount of trifluoroacetic acid (0.056 mL), and the reaction mixture was stirred for four hours at room temperature. The solution was then washed with a saturated solution of sodium bicarbonate and brine, and dried over magnesium sulfate. The crude oil obtained after evaporating the solvent, was purified by chromatography on silica gel using hexane:ethyl acetate 1:1 as a solvent, giving 2.6 g of (R)-5-(1-ethoxy-ethoxymethyl)-3,3-dimethyl-pyrrolidin-2-one.

Workup

  1. washThe solution was then washed with a saturated solution of sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude oil obtained
  4. customafter evaporating the solvent
  5. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9915ae513afa47158494a076450f7fa0
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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