Triethylamine → Etiracetam, (R)-

HRID 601728Notes

Reaction equation

HRID 601728 reaction equation
[CH2:1]([C@@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[C:4](O)=[O:5])[CH3:2].C([N:15](CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH2:1]([C@@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[C:4]([NH2:15])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 116007472-(2-Oxopyrrolidin-1-yl)butanoic acid, (2R)-

Product 1

HCID 441341Etiracetam, (R)-Yield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (R)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid (35 g, 0.20 mol) in methylene chloride (225 ml) was cooled to 0° C. and triethylamine (41 g, 0.40 mol) and methanesulfonyl chloride (29 g, 0.26 mol) were added dropwise. The mixture was stirred at 0° C. for 30 min., then a stream of ammonia was purged in the solution at 0° C. for 2 hours. The insoluble solids were filtered and the filtrate was concentrated. The product was recrystallized from methyl isobutyl ketone to give 27.5 g (78%) of (R)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide.

Workup

  1. customa stream of ammonia was purged in the solution at 0° C. for 2 hours
  2. filtrationThe insoluble solids were filtered
  3. concentrationthe filtrate was concentrated
  4. customThe product was recrystallized from methyl isobutyl ketone

Sources & evidence

ORD record
ord-fe3d671ac3dd48b7a8e1e125bcf09ad2
Source dataset
uspto-grants-2011_03
Patent number
US07902380B2

Reaction notes

Loading…