61422-43-3

Upstream product

• 111-49-9 hexamethylene imine 
• 108-94-1 cyclohexanone 
• 60-32-2 6-aminohexanoic acid 
• 1072-21-5 hexanedial 
• 108-91-8 cyclohexylamine 

Relevant academic research and scientific papers

Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines

An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

N-alkylation of amines under microwave irradiation: Modified eschweiler-clarke reaction

The N-alkylation of hexahydroazepine and benzylamine is performed under microwave irradiation in the presence of formic acid and different aldehydes or ketones. Good yields were obtained with reactive carbonyl compounds.

A New and Convenient Synthesis of N-Substituted Perhydroazepines from Adipaldehyde and Primary Amines with Tetracarbonylhydridoferrate, HFe(CO)4-, as a Selective Reducing Agent

Ethanolic tetracarbonylhydridoferrate combined with adipaldehyde is very efficient for the selective transformation of an amino group into perhydroazepine.A large variety of both aliphatic and aromatic amines react with adipaldehyde in the presence of tetracarbonylhydridoferrate at room temperature and carbon monoxide to give the corresponding N-alkyl- and N-arylperhydroazepines in good to excellent yields.