[zq]

Is there a method to selectively reduce an ethyl ester (to an alcohol) in the presence of an amide linkage? Something milder than NaBH4 should work.

[sjb]

I've mentioned this paper before on here, have not tried in vitro, so don't know how sucessful it is.

ARKIVOC 2001 (iv) 59-75 ( http://www.arkat-usa.org/get-file/18729/ ), scheme 1, part 2 uses LiBH₃NMe₂, at low temp to reduce a methyl ester in the prescence of a lactam.

What sort of amide link are we talking about?

S

[zq]

I have seen that paper. Thanks.

The amide is part of a 3,4-dihydroquinolin-2(1H)-one system.

[pngeneric]

u can go with sncl2 HCl

[Custos]

I'd try sodium cyanoborohydride.

[diangeloz]

what's the problem with sodium borohydride? What solvent did you use? It should do the job, you could also add cerium chloride to enhance the reactivity.  Sodium triacetoxyborohydride is also usefull.