Acetic Anhydride → Rolziracetam

HRID 978197

Reaction equation

HRID 978197 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C(OC(=O)C)(=O)C>C(O)(C)C>[CH2:4]1[CH:5]2[N:6]([C:9](=[O:11])[CH2:8][CH2:7]2)[C:2](=[O:1])[CH2:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 45856673-(5-Oxopyrrolidin-2-yl)propanoic acid

Product 1

HCID 71893RolziracetamYield 89.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

5-Oxo-2-pyrrolidinepropanoic acid (15.7 g, 0.1 mol) was added to 45 ml of acetic anhydride and the mixture was heated slowly to 90° C. and held at that temperature for six hours. The mixture was cooled and the volatile materials stripped off at a temperature of 60° C. under vacuum. The residue (14.2 g) was dissolved in 230 ml of isopropyl alcohol, the solution decolorized, filtered, and concentrated to 30 ml. This solution was cooled 0°-5° C. for two hours, and the solid which separated was collected by filtration, washed twice with 25-ml portions of isopropyl alcohol to yield 12.5 g (89.9%) of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione, mp 180.2°-181.8° C. which was found to be 99.5% pure by high pressure liquid chromatographic (HPLC) analysis.

Workup

  1. temperatureThe mixture was cooled
  2. customstripped off at a temperature of 60° C. under vacuum
  3. filtrationfiltered
  4. concentrationconcentrated to 30 ml
  5. temperatureThis solution was cooled 0°-5° C. for two hours
  6. customthe solid which separated
  7. filtrationwas collected by filtration
  8. washwashed twice with 25-ml portions of isopropyl alcohol

Sources & evidence

ORD record
ord-c2699f9eb79c48e49fb583a9c5f35a39
Source dataset
uspto-grants-1987_05
Patent number
US04663464

Linked notes

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