Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines

Advanced Synthesis and Catalysis

Volumn 353, Issue 11-12, 2011, Pages 2085-2092

  Nugent, Thomas C ^a   Negru, Daniela E ^a   El Shazly, Mohamed ^a   Hu, Dan ^a   Sadiq, Abdul ^a   Bibi, Ahtaram ^a   Umar, M Naveed ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

asymmetric reductive amination; chiral amines; hydrogenolysis; primary amine synthesis

Indexed keywords

EID: 80052018660     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100250     Document Type: Article

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75. 1,2-Dichloroethane is the optimal reaction solvent, but transfer of the Raney-Ni slurry into the reaction with this solvent (via a wide gauge needle and syringe) was not feasible due to the technical problem that 1,2-dichloroethane slurries of Raney-Ni were not free-flowing. This was overcome by using a toluene slurry (see the Supporting Information). Fortunately, the toluene did not adversely affect the positive attributes of 1,2-dichloroethane solvent.
76. The aliphatic primary amine 3e was of lower chemical purity, 88 area% (GC), after work-up. It was consequently chromatographed before the yield was calculated. All primary amines (3) are semi-volatile to volatile, see the Supporting Information for the method of careful chromatography of 3e.
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