methyl-(R)-4-(1-carbamoylpropylamino)butyrate → Etiracetam, (R)-

HRID 2197663Notes

Reaction equation

HRID 2197663 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][NH:7][C@@H:8]([C:11](=[O:13])[NH2:12])[CH2:9][CH3:10]>C1(C)C=CC=CC=1>[O:2]=[C:3]1[CH2:4][CH2:5][CH2:6][N:7]1[C@H:8]([CH2:9][CH3:10])[C:11]([NH2:12])=[O:13]

Participants

3

Reactant 1

HCID 59650081methyl-(R)-4-(1-carbamoylpropylamino)butyrate

Product 1

HCID 441341Etiracetam, (R)-Yield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To the crude methyl-(R)-4-(1-carbamoylpropylamino)butyrate (VIf) in toluene (20 ml) is added 2-hydroxypyrridine (50 mg, 10 mol %). The mixture is heated to 80° C. until complete conversion. After 16 hours (GC: 100% conversion) the mixture is concentrated to dryness to yield (R)-2-(2-oxopyrrolidin-1-yl)butyramide (0.28 g, 1.6 mmol, 30%, yield determination by GC assay from pure standard).

Workup

  1. concentrationAfter 16 hours (GC: 100% conversion) the mixture is concentrated to dryness

Sources & evidence

ORD record
ord-4366f7dfe47c471d9ff801267fc62ee2
Source dataset
uspto-grants-2012_12
Patent number
US08338621B2

Reaction notes

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