ORGLIST:Reductive Amination, summary of replies.

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From: Andrea Giordano (giordano$##$embl.de)
Date: Sun May 25 2003 - 08:43:41 EDT

I would like to thank the people who gave their contribute with suggestions on
my topic posted days ago.

Here's a list of suggested methods:

- NH3 + reductive agent such NaBH4 (sometimes risky toward -NO2) or NaCNBH3;
- reduct. of -CHO to -CH2OH (NaBH4, risky toward -NO2), transform. the OH into
bromide or tosylate, introduction N3 and reduct. of N3 by using Ph3P;
- trasf. -CHO into -CH=N-OH by hydroxylamine, then reduct. with methallic
sodium in MeOH or with NaBH4;
- trasf. -CHO into -CH=N-R by a suitable amine, then reduction. with methallic
sodium in MeOH or with NaBH4;
- ammonium acetate & NaCNBH3;

suggested references:
Tetrahedron, 2001, vol. 57, p. 6197
Gross, Seayad et al., Org.Lett.; EN; 4; 12; 2002; 2055 - 2058

By the way, Na(OAc)3BH has been described as a mild reducing agent with no
toxic byproducts compared to NaCNBH3 (JOC, v.61, pp. 3849-3862, 1996), and I
will go for this one to start...

Cheers, 

-- 
Andrea Giordano
PhD student, Schultz group 
Gene Expression Program
EMBL
Meyerhofstrasse, 1 
69117 Heidelberg, Germany
tel: 0049 6221 387 498
fax: 0049 6221 387 206

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