[pallidol]

Hi guys,

I would like to ask your opinion regarding my work. I have reduced my compound using sodium borohydride and obtained two products. The first product showed that the reduction did not work for carbonyl at C-5 position and for the second product it showed to be reduced. For the second product it is understood that only one of the carbonyl next to nitrogen group played an amide functionality.

Is this common in reducing using sodium borohydride because i could not find any literature regarding this. Could anybody assists me in this matter. Tq

[Dan]

After the first reduction, you have a cyclic imide (not an amide).

Imide reduction with NaBH₄ is known, see for example:

http://www.sciencedirect.com/science/article/pii/0040402075870761

[orgopete]

If you reduce succinimide or phthalimidevwith borohydride, the first reduction gives a similar aminal. It also opens to the aldehyde amide and is reduced again to the alcohol amide. I thought it interesting the reference given by Dan used a combination of HCl and NaBH4. That is unusual for borohydride reductions.

[Anil9494]

 please help me to workup procedure of cyclic imide reduction with nabh4 and h2so4

[discodermolide]

I seem to remember that NaBH₄ and mineral acids produce diborane. So I would be careful .