[IsotopeBill]

I'm looking for various methods of reducing a nitrile in the presence of a t-butyl ester.  Borane has resulted in reduction of the ester (acid chlorides are supposed to be inert to borane.  perhaps proceed via the acid chloride rather than the ester?).  Pt/Pd reduction was successful, but caused problems elsewhere nad so cannot be used.

Any suggestions (esp. w/ lit. references) would be greatly appreciated

[sjb]

I'm looking for various methods of reducing a nitrile in the presence of a t-butyl ester.  Borane has resulted in reduction of the ester (acid chlorides are supposed to be inert to borane.  perhaps proceed via the acid chloride rather than the ester?).  Pt/Pd reduction was successful, but caused problems elsewhere nad so cannot be used.

Any suggestions (esp. w/ lit. references) would be greatly appreciated

What's the next step? Presumably the free amine may react with the acid chloride, so this doesn't sound useful; unless you plan making the lactam and then hydrolysing that and reforming the amino ester?

[IsotopeBill]

This is actually the last step - we want the amino ester.  I actually don't like the acid chloride idea because it may cause other issues.  I'm really mostly interested in various reduction processes, hoping to find an example that's promising.  There's a lot of recent activity using SmI2 and related reagents, but they seem to target the esters at least as much as the nitriles.

[Dan]

Ni(II)-catalysed borohydride reduction perhaps?

See Table 1, entry 27 here:

http://www.sciencedirect.com/science/article/pii/S0040402003008585

I expect this to reduce alkenes though - and I'm guessing you have something hydrogenation sensitive since you mentioned Pt/Pd reduction caused problems somewhere (and that you've not mentioned Raney Ni/H₂).

[IsotopeBill]

Thanks for the paper.  I had also come across a CoCl2-NaBH4 article