Hydrochloric Acid → Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

HRID 46428Notes

Reaction equation

HRID 46428 reaction equation
C[Si](C)(C)OC1CNC(=O)C1.BrCC(OCC)=O.[H-].[Na+].C[Si](C)(C)[O:23][CH:24]1[CH2:28][N:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:26](=[O:35])[CH2:25]1.Cl>C(#N)C>[OH:23][CH:24]1[CH2:28][N:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:26](=[O:35])[CH2:25]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 150784244-[(Trimethylsilyl)oxy]pyrrolidin-2-oneHCID 20387060HCID 20387060, compound

Product 1

HCID 12365604Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 51.5 g. 4-trimethylsilyloxypyrrolidin-2-one in 500 ml. anhydrous acetonitrile are added 133 ml. ethyl bromoacetate. The solution is heated to 50° C. and 26.7 g. of 80% sodium hydride (dispersion in mineral oil) are slowly added in small amounts. When the addition is completed, the reaction mixture is heated under reflux for 30 minutes and then cooled to ambient temperature. To the reaction mixture obtained containing ethyl 2-(4-trimethylsilyloxypyrrolidin-2-on-1-yl)-acetate (b.p. 160° C./3 mm.Hg) are added 50 ml. 1 N hydrochloric acid. The reaction mixture is stirred for 30 minutes and then evaporated to dryness. The residue obtained is chromatographed on a silica gel column, using ethyl acetate as the elution agent, 45 g. ethyl 2-(4-hydroxypyrrolidin-2-on-1-yl)-acetate being obtained; b.p. 180° C./0.8 mm.Hg; Rf 0.17 (silica gel; eluant ethyl acetate).

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled to ambient temperature
  5. customTo the reaction mixture obtained
  6. additionare added 50 ml
  7. customevaporated to dryness
  8. customThe residue obtained
  9. customis chromatographed on a silica gel column

Sources & evidence

ORD record
ord-6cd2aa9101a242dfb07a8331b1775939
Source dataset
uspto-grants-1979_11
Patent number
US04173569

Reaction notes

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