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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: zq on April 02, 2008, 11:43:51 PM

Title: selective reduction
Post by: zq on April 02, 2008, 11:43:51 PM
How can you selectively reduce ethyl ester of an aromatic carboxylic acid in the presence of a 6-membered lactam (amide) fused with the aromatic ring. I got 22% yield of the target benzyl alcohol by using NaBH4. There are side products arising from reduction of amide group.
Title: Re: selective reduction
Post by: sjb on April 03, 2008, 04:00:04 AM
A quick FWSE has given this, but I can't work out what paper it's from at the minute (so no precise details  :( )

http://acsinfo.acs.org/isubscribe/journals/oprdfk/10/i05/figures/op0600759h00020.html (http://acsinfo.acs.org/isubscribe/journals/oprdfk/10/i05/figures/op0600759h00020.html)
Title: Re: selective reduction
Post by: sjb on April 03, 2008, 11:05:13 AM
Quote from: sjb on April 03, 2008, 04:00:04 AM
A quick FWSE has given this, but I can't work out what paper it's from at the minute (so no precise details  :( )

http://acsinfo.acs.org/isubscribe/journals/oprdfk/10/i05/figures/op0600759h00020.html (http://acsinfo.acs.org/isubscribe/journals/oprdfk/10/i05/figures/op0600759h00020.html)

Just a quick follow-up, perhaps http://www.arkat-usa.org/get-file.php?fileid=18729 (http://www.arkat-usa.org/get-file.php?fileid=18729) (Aminoborohydrides. 13. Facile reduction of N-alkyl lactams with 9-borabicyclo[3.3.1]nonane (9-BBN) and lithium aminoborohydrides (LAB) reagents (AH-179CP)
Christopher J. Collins and Bakthan Singaram) is of use?
Title: Re: selective reduction
Post by: zq on April 03, 2008, 03:28:57 PM
Thank you very much. I met a person from Singaram's group yesterday. She was saying it cannot be done with LAB reagents. But the reference you provided seems useful.