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Topic: Synthesis of an analgesic  (Read 1391 times)

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Offline Dee

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Synthesis of an analgesic
« on: April 11, 2013, 02:19:58 PM »

I have proposed this particular reaction for the synthesis of a naturally occurring compond "Epibatadine" an analgesic.

I would like to discuss on its synthetic strategy.

Thanks.
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Offline Schrödinger

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Re: Synthesis of an analgesic
« Reply #1 on: April 18, 2013, 05:20:02 AM »
I have seen cyclopentadiene being used for a Diels-Alder. But pyrrole is aromatic. So, I don't know to what extent this is feasible (unless you've verified the reaction from some source)
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Offline AWK

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Re: Synthesis of an analgesic
« Reply #2 on: April 18, 2013, 06:33:15 AM »
Diels-Alder reaction of N-BOC pyrrole and methyl pyrrole-1-carboxylate were used in synthesis of epibatidine.

see Tetrahedron Letters Volume 34, Issue 46, 12 November 1993, Pages 7493–7496
J. Org. Chem. 1996, 61, 7989-7191
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