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Topic: amide to amino alcohol  (Read 4780 times)

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Offline absbhai

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amide to amino alcohol
« on: January 23, 2008, 07:43:08 AM »
hi. I want to reduce an amide to amino alcohol. How can i stop the reaction before the amide can end up as amine?

Offline sjb

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Re: amide to amino alcohol
« Reply #1 on: January 24, 2008, 02:45:28 AM »
I'm a little confused as to what you mean here, first you want to reduce the amide to an amino alcohol, then without forming the amine??

Do you mean a 1,1-aminoalcohol (a bit like RCONHR'R'' -> RCH(OH)NR'R'' ) with the alcohol and amine on the same carbon?

Offline absbhai

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Re: amide to amino alcohol
« Reply #2 on: January 24, 2008, 08:37:52 AM »
sorry mate. i guess i got the wrong nomenclature. What i want is to reduce the amide to aminal. something like RC(O)NHMe to RCH(OH)NHMe. the standard procedures for reduction that i was able to dig up, all lead to the formation of an amine RCH2NHMe. Any sugesstions please

Offline AWK

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Re: amide to amino alcohol
« Reply #3 on: January 24, 2008, 11:50:39 AM »
You have little or no chance. Aminals with free OH groups are extremely unstable.
AWK

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