ORGLIST: Nitrile to methylamino

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From: Jacobo Cruces (jacobo.cruces$##$
Date: Tue Nov 30 2004 - 12:25:08 EST

Dear all,

We are looking for a selective method of reducing a nitrile to methylamio
in a molecule with several acetoxi groups and a double bond. We have
considered using NaBH4 in the presence of CoCl2. However, a paper of Ganem
et al. (J. Am. Chem. Soc. 1982, 104, 6801) states that this method can also
reduce double and triple bonds. Unlike other methods recently suggested on
this list (NaBH4 in presence of Li, Zn or Ca) this method does not reduce
esters (see for example Organic Letters 2001, 3, 2081).

Can anyone suggest a mild, selective method for reducing a CN to CH2NH2 in
the presence of esters and double bonds?

Best regards,

Visit us at ICSE in Brussels next December 7-9, Stand 9443 - Hall 9C

Dr. Jacobo Cruces
Research Manager
GalChimia, S.L.
Cebreiro, s/n O Pino
15823 A Coruņa

Phone: +34 981 814 506
Fax: +34 981 814 507

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