824938-91-2

Upstream product

• 18468-90-1 (+/-)-trans-2-(piperidin-1-yl)cyclohexanamine 
• 141-78-6 ethyl acetate 
• 111-24-0 1,5-dibromo-pentane 
• 320778-89-0 N-((1R,2R)-2-aminocyclohexyl)acetamide 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 7581-94-4 trans-2-(pipoeridin-1-yl)cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 110-89-4 piperidine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 885677-91-8 (1R,2R)-N¹-piperidinyl-1,2-diaminocyclohexane 

Relevant academic research and scientific papers

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: Possible route to the 4-methylpregabalin core structure

Chiral derivatives of γ-aminobutyric acid are widely used as medicines and can be obtained by organocatalytic Michael additions. We show here the stereoselective synthesis of 4-methylpregabalin stereoisomers using a Michael addition of dimethyl malonate to a racemic nitroalkene. The key step of the synthesis operates as a kinetic resolution with a chiral squaramide catalyst. Furthermore, specific organocatalysts can provide respective stereoisomers of the key Michael adduct in up to 99:1 er.

Enantioselective Michael addition of 1,3-dicarbonyl compounds to a nitroalkene catalyzed by chiral squaramides-a key step in the synthesis of pregabalin

Asymmetric organocatalytic 1,4-additions provide access to a large number of biologically relevant compounds. Chiral squaramides efficiently catalyse enantioselective Michael addition of 1,3-dicarbonyl compounds to aliphatic nitroalkenes. The resulting γ-

Chemoenzymatic preparation of optically active trans-cyclohexane-1,2- diamine derivatives: An efficient synthesis of the analgesic U-(-)-50,488

Stereoespecific syntheses of (±)-trans-N,N-cyclohexane-1,2-diamines ((±)-4a-g) were carried out from the corresponding (±)-trans-N,N- dialkylaminocyclohexanols by successive treatment with mesyl chloride and aqueous ammonia. The stereochemical outcome indicates the formation of a meso-aziridinium ion intermediate, Kinetic resolutions of diamines (±)-4 were efficiently accomplished in aminolysis reactions catalyzed by lipase B from Candida antarctica with ethyl acetate as the solvent and acyl donor. Acetamides and the remaining diamines, isolated as the benzyloxycarbonyl derivatives, were obtained with very high ee values (92-99%), One of the carbamates was used as a precursor of the analgesic U-(-)-50,488.