An alternate synthesis of enantiomerically pure levetiracetam (Keppra®)

A simple and efficient synthesis of levetiracetam has been achieved with high enantiopurity (>99%) starting from commercially available benzyl glycidyl ether. The method is amenable for industrial scale-up.

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(R)-2-((Benzyloxy)methyl)oxiraneC10H12O2[α]D25=-7.9 (c 0.4, EtOH)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)

(R)-1-(Benzyloxy)butan-2-olC11H16O2[α]D25=-9.5 (c 0.8, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)

(S)-1-(1-(Benzyloxy)butan-2-yl)pyrrolidine-2,5-dioneC15H19NO3[α]D25=+31.5 (c 3.1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(S)-1-(1-(Benzyloxy)butan-2-yl)pyrrolidin-2-oneC15H21NO2[α]D25=-30.5 (c 1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(S)-1-(1-Hydroxybutan-2-yl)pyrrolidin-2-oneC8H15NO2[α]D25=-20.1 (c 1.1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(S)-2-(2-Oxopyrrolidin-1-yl)butanoic acidC8H13NO3[α]D25=-27.1 (c 1.1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(S)-2-(2-Oxopyrrolidin-1-yl)butanamideC8H14N2O2[α]D25=-91.5 (c 1, acetone)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)