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14891857Racemization of S-(+)-PZQamine with Pd/C (MW50-1 to MW50-3)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle no decomposition / side reaction of the starting material [b]MW50-3[/b] 1% Pd, 2 h [α]D20 = +152° (c=1, DCM) [b]Results:[/b] - slow racemization of S-(+)-PZQamine with 1% Pd/C under the conditions stated above -> increase of temperature and catalyst loading (5% Pd) [b]References:[/b] [1] "Fast racemization and dynamic kinetic resolution of primary benzyl amines", Y. Kim, J. Park and M.-J. Kim, Tetrahedron Letters [b]2010[/b],[i]51[/i], 42, 5581-5584, [url=http://dx.doi.org/10.1016/j.tetlet.2010.08.050](http://dx.doi.org/10.1016/j.tetlet.2010.08.050)[/url] [2] "Lipase/Palladium-Catalyzed Asymmetric Transformations of Ketoximes to Optically Active Amines", Y. K. Choi, M. J. Kim, Y. Ahn, and M.-J. Kim, [i]Org. Lett.[/i] [b]2001[/b], [i]3[/i], 25, 4099–4101; [url=http://dx.doi.org/10.1021/ol0168622]DOI: 10.1021/ol0168622[/url]]]>S-(+)-PZQamine with Pd/C obtained from Multigram-scale racemic resolution of praziquanamine with (-)-Dibenzoyl-L-tartaric acid (MW49-13)

Scheme MW50-1.png


See also:
  • Racemization of S-(+)-PZQamine with Pd/C (MW50-4)
  • Racemization of S-(+)-PZQamine with Pd/BaSO4 (MW50-5)
  • Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)
  • Thiyl radical-mediated racemization of S-(+)-PZQamine (MW50-8)

    Hazard and Risk Assessment:
  • HRAF MW50.pdf


    Start time: 3:50 PM 17/01/2011
    End time: 1:40 PM 18/01/2011

    To a solution of S-(+)-PZQamine (50 mg, 248 µmol, MW: 202.3 g/mol) in toluene (5 mL) was added Pd/C (for 1% Pd: 2.62 mg, 2.48 µmol; for 5% Pd: 13.1 mg, 12.4 µmol; 10% Pd on charcoal, M.W. (Pd) 106.4 g/mol) and heated to 70°C for 3 / 22 h.
    The catalyst was filtered off by a filter paper and the solvent was evaporated.

    Notes:
    - almost complete amount of starting material was reisolated
    - color of the starting material turned from pale yellow to yellow

    Starting material S-(+)-PZQamine
    [α]D20 = +170° (c=1, DCM)

    MW50-1
    1% Pd, 3 h
    [α]D20 = +156° (c=1, DCM)

    MW50-2
    5% Pd, 3 h
    [α]D20 = +131° (c=1, DCM)
    Data: 1H NMR MW50-2.pdf
    -> no decomposition / side reaction of the starting material

    MW50-3
    1% Pd, 2 h
    [α]D20 = +152° (c=1, DCM)


    Results:
    - slow racemization of S-(+)-PZQamine with 1% Pd/C under the conditions stated above
    -> increase of temperature and catalyst loading (5% Pd)

    References:
    [1] "Fast racemization and dynamic kinetic resolution of primary benzyl amines", Y. Kim, J. Park and M.-J. Kim, Tetrahedron Letters 2010,51, 42, 5581-5584, (http://dx.doi.org/10.1016/j.tetlet.2010.08.050)

    [2] "Lipase/Palladium-Catalyzed Asymmetric Transformations of Ketoximes to Optically Active Amines", Y. K. Choi, M. J. Kim, Y. Ahn, and M.-J. Kim, Org. Lett. 2001, 3, 25, 4099–4101;
    DOI: 10.1021/ol0168622
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    14896950Racemization of S-(+)-PZQamine with Pd/C (MW50-1 to MW50-3)
    Experiments
    profiles.google.com-micha.wolfleMichael Wolfle no decomposition / side reaction of the starting material [b]MW50-3[/b] 1% Pd, 2 h [α]D20 = +152° (c=1, DCM) [b]Results:[/b] - slow racemization of S-(+)-PZQamine with 1% Pd/C under the conditions stated above -> increase of temperature and catalyst loading (5% Pd) [b]References:[/b] [1] "Fast racemization and dynamic kinetic resolution of primary benzyl amines", Y. Kim, J. Park and M.-J. Kim, Tetrahedron Letters [b]2010[/b],[i]51[/i], 42, 5581-5584, [url=http://dx.doi.org/10.1016/j.tetlet.2010.08.050](http://dx.doi.org/10.1016/j.tetlet.2010.08.050)[/url] [2] "Lipase/Palladium-Catalyzed Asymmetric Transformations of Ketoximes to Optically Active Amines", Y. K. Choi, M. J. Kim, Y. Ahn, and M.-J. Kim, [i]Org. Lett.[/i] [b]2001[/b], [i]3[/i], 25, 4099–4101; [url=http://dx.doi.org/10.1021/ol0168622]DOI: 10.1021/ol0168622[/url]]]>S-(+)-PZQamine with Pd/C obtained from Multigram-scale racemic resolution of praziquanamine with (-)-Dibenzoyl-L-tartaric acid (MW49-13)

    Scheme MW50-1.png


    See also:
  • Racemization of S-(+)-PZQamine with Pd/C (MW50-4)
  • Racemization of S-(+)-PZQamine with Pd/BaSO4 (MW50-5)
  • Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)
  • Thiyl radical-mediated racemization of S-(+)-PZQamine (MW50-8)

    Hazard and Risk Assessment:
  • HRAF MW50.pdf


    Start time: 3:50 PM 17/01/2011
    End time: 1:40 PM 18/01/2011

    To a solution of S-(+)-PZQamine (50 mg, 248 µmol, MW: 202.3 g/mol) in toluene (5 mL) was added Pd/C (for 1% Pd: 2.62 mg, 2.48 µmol; for 5% Pd: 13.1 mg, 12.4 µmol; 10% Pd on charcoal, M.W. (Pd) 106.4 g/mol) and heated to 70°C for 3 / 22 h.
    The catalyst was filtered off by a filter paper and the solvent was evaporated.

    Notes:
    - almost complete amount of starting material was reisolated
    - color of the starting material turned from pale yellow to yellow

    Starting material S-(+)-PZQamine
    [α]D20 = +170° (c=1, DCM)

    MW50-1
    1% Pd, 3 h
    [α]D20 = +156° (c=1, DCM)

    MW50-2
    5% Pd, 3 h
    [α]D20 = +131° (c=1, DCM)
    Data: 1H NMR MW50-2.pdf
    -> no decomposition / side reaction of the starting material

    MW50-3
    1% Pd, 2 h
    [α]D20 = +152° (c=1, DCM)


    Results:
    - slow racemization of S-(+)-PZQamine with 1% Pd/C under the conditions stated above
    -> increase of temperature and catalyst loading (5% Pd)

    References:
    [1] "Fast racemization and dynamic kinetic resolution of primary benzyl amines", Y. Kim, J. Park and M.-J. Kim, Tetrahedron Letters 2010,51, 42, 5581-5584, (http://dx.doi.org/10.1016/j.tetlet.2010.08.050)

    [2] "Lipase/Palladium-Catalyzed Asymmetric Transformations of Ketoximes to Optically Active Amines", Y. K. Choi, M. J. Kim, Y. Ahn, and M.-J. Kim, Org. Lett. 2001, 3, 25, 4099–4101;
    DOI: 10.1021/ol0168622
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