java
(Hive Bee)
08-06-03 05:07
No 451980
      Reductive Amination of Ketones and aldehydes...
(Rated as: excellent)
    

Reductive Amination of Ketones and aldehydes with Hydrazine Using BorohydrideExchange Resin (BER)-Nickel Acetate in Methanol

Bull. Korean Chem. Soc. Vol.19, No.2, 269-270,1998
Jae Hou Nah, Suk Youn Kim, and Nung Min Yoon

http://journal.kcsnet.or.kr/publi/bul/bu98n2/269.pdf

Excerp..

....."Recently , we have reported that BER-Ni(OAc)2 in methanol is an excellent reducing system for azides and nitro compounds "

...in summary, the synthesis of primary amines by the present method is a good alternative to the cyanoborohydride method which is expensive and toxic, and may be much more convenient than catecholborane-Raney Ni reduction.


Edit: direct link fixed

We're  all in this world together,
 http://www.chiapaslink.ukgateway.net/
 
 
 
 
    Rhodium
(Chief Bee)
08-06-03 05:46
No 451992
      I wonder...     

Nice article, but why didn't you link it directly and write out the full reference?

Reductive Amination of Ketones and Aldehydes with Hydrazine Using Borohydride Exchange Resin (BER)-Nickel Acetate in Methanol
Jae Hou Nah, Suk Youn Kim, and Nung Min Yoon
Bull. Korean Chem. Soc. 19(2), 269-270 (1998) (http://journal.kcsnet.or.kr/publi/bul/bu98n2/269.pdf)
 
 
 
 
    Rhodium
(Chief Bee)
11-23-03 23:53
No 472724
      Reductive Amination: Borohydride Exchange Resin
(Rated as: excellent)
    

Borohydride Exchange Resin, A New Reducing Agent for Reductive Amination
Nung Min Yoori , Eui Gyun Kim, Heui Sung Son and Jaesung Choi
Synth. Commun. 23(11), 1595-1599 (1993) (../rhodium/chemistry /redamin.ber.html)

Abstract
Borohydride Exchange Resin is a useful, convenient reducing agent for the reductive amination of aldehydes and ketones in alcoholic solvent.
 
 
 
 
    java
(Hive Bee)
11-24-03 00:45
No 472733
      Re: Borohydride Exchange Resin (BER)....     

Selective reduction of mixed anhydrides of carboxylic acids to alcohols
 using borohydride exchange resin (BER)-nickel acetate

B. P. Bandgar, R. K.; Modhave, P. P. Wadgaonkar and A. R. Sande

Perkins Transactions 1,Issue 16,pg.1997, (1996)

Note: No abstract available, article would be welcomed as it may be an interesting alternative to reduction of Phenylalanine to Phenylalinol

We're  all in this world together,
http://www.aztlan.net
 
 
 
 
    Rhodium
(Chief Bee)
01-06-04 23:02
No 480801
      BER-Ni(OAc)2 Anhydride -> Alcohol Reduction
(Rated as: good read)
    

Selective reduction of mixed anhydrides of carboxylic acids to alcohols using borohydride exchange resin (BER)-nickel acetate
B. P. Bandgar, R. K.; Modhave, P. P. Wadgaonkar and A. R. Sande
J. Chem. Soc. Perkin Trans 1, 1993-1994 (1996) (../rhodium/pdf /ber.ni-acetate.pdf)

Abstract
Mixed anhydrides of carboxylic acids have been selectively reduced to alcohols with borohydride exchange resin and nickel acetate under mild conditions and in good yields.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    gsus
(Hive Bee)
03-07-04 10:50
No 493569
      more from korea
(Rated as: good read)
    

actually it was foxy2 who found that 1st ref., coupla years ago. it keeps getting rediscovered! but theres more - a related high yielding, simpler reaction was published 9 issues later. this is an application of the '93 article, using only dimethylamine as amine. they used a small number of substrates and only in sub-gram amts. as well, so this is of dubious Hive usefulness. that said - indoleacetaldehyde? indoleacetone and (the rarely mentioned) a-N,N-TMT?
  Reductive Amination of Aldehydes and Ketones with Dimethylamine Using Borohydride Exchange Resin (BER)
  by Lee, Cho, and Yoon. Bull. Kor. Chem. Soc. 1998 vol.19, #11 pg.1268
http://journal.kcsnet.or.kr/publi/bul/bu98n11/1268.pdf
  an aldehyde or ketone is mixed with EtOH solvent, dimethylamine in EtOH, triethylamine HCl, and BER. this is stirred for an hour or two at RT and the N,N-dimethylamine'd product is isolated in high yield.
  like the other articles, they didnt do this to anything interesting. the substrates that were used do demonstrate good selectivity, however. btw, has anyone heard of the 1st article being used with P2P? perhaps b4 the product was N-methylated? didnt think so. what about a substituted phenylacetaldehyde?
  and in the '93 article, what would you get if ammonium formate was used instead of acetate? i also note methylamine was not used. well, why not?