CYCLODOL

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SionK - 01 Feb 2006 08:47 GMT

Hi
Can anyone help me to this synthesis:
*
Ph(C6H5)-C(OH)-(cyclohexan)
/
CH2 - CH2 - (PIPERIDINE=C6H10N)
(starting from compounds with no more than 3 carbons)

SORRY THAT I CAN'T POST THE IMAGE SINCE THE GROUP IS USENET

I don't really know the name of this compound (may be "cyclodol")

Thanks a lot

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Gabriel Tojo - 07 Feb 2006 08:53 GMT

I would consider using the following reactions:

For the piperidine ring: conjugated addition of amonia on an acrylic
acid derivative, followed by 1- transformation to diester and Dickmann
cyclization, and 2- hydrolisys and decarboxylation.

The piperidine molecule could then be reacted again with an acrylic
acid derivative.

After adjusting the oxidation state to aldehyde, the resulting aldehyde
could be reactied with an organometallic compound. The resulting
alcohols could be oxidized to ketone. Addition of another
organometallic compound would deliver the final compound.

Best regards.

Gabriel Tojo

Consultant in Organic Synthesis

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Natural Science Forum / Chemistry / Organic Synthesis / February 2006

CYCLODOL