New Method for Preparation of ( ) - 1,2,3,4-Tetrahydropapaverine
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    Abstract:

    Merrified resin-bound BINOL–derived phosphoric acid has been employed for the catalytic transfer hydrogenation of 3,4-dihydropapaverine to synthesize ( )-1,2,3,4-tetrahydropapaverine. Several catalysts were selected and the excellent catalyst was bounded on Merrified resin. The effects of solvent type, reaction temperature and structure of Hantzsch ester on yield and ee value of ( )-1,2,3,4-tetrahydropapaverine are investigated in detail. Under the optimal conditions (toluene as solvent, 40℃ and dimethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as hydride source), the ( )-1,2,3,4-tetrahydropapaverine was obtained in 95% yield and 98% ee. The catalyst can be easily separated and recycled. After reused seven times, the activity of catalyst was observed a small drop in ee, but can regained by simple cleaning in hydrogen chloride - ethyl acetate solution.

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History
  • Received:October 10,2015
  • Revised:November 23,2015
  • Adopted:December 01,2015
  • Online: December 16,2015
  • Published:
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