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selective reduction
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Topic: selective reduction (Read 8358 times)
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zq
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selective reduction
«
on:
May 07, 2008, 01:22:59 PM »
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.
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sjb
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Re: selective reduction
«
Reply #1 on:
May 07, 2008, 02:17:56 PM »
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 LiBH
3
NMe
2
, at low temp to reduce a methyl ester in the prescence of a lactam.
What sort of amide link are we talking about?
S
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zq
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Re: selective reduction
«
Reply #2 on:
May 07, 2008, 02:19:40 PM »
I have seen that paper. Thanks.
The amide is part of a 3,4-dihydroquinolin-2(1H)-one system.
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pngeneric
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Re: selective reduction
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Reply #3 on:
May 29, 2008, 04:47:18 AM »
u can go with sncl2 HCl
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Custos
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Re: selective reduction
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Reply #4 on:
June 03, 2008, 10:09:59 PM »
I'd try sodium cyanoborohydride.
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diangeloz
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Re: selective reduction
«
Reply #5 on:
October 23, 2008, 11:44:51 AM »
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.
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selective reduction