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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: absbhai on January 23, 2008, 07:43:08 AM

Title: amide to amino alcohol
Post by: absbhai 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?

Title: Re: amide to amino alcohol
Post by: sjb 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?

Title: Re: amide to amino alcohol
Post by: absbhai 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

Title: Re: amide to amino alcohol
Post by: AWK on January 24, 2008, 11:50:39 AM

You have little or no chance. Aminals with free OH groups are extremely unstable.