476014-78-5

Upstream product

• 147028-51-1 4-cyano-3-hydroxybutanoic acid 
• 476014-76-3 (±)-4-hydroxypiperidin-2-one 
• 158849-52-6 4-cyano-3-hydroxybutyric acid methyl ester 
• 79-22-1 methyl chloroformate 
• 476014-77-4 (±)-4-((tert-butyldiphenylsilyl)oxy)piperidin-2-one 
• 17640-15-2 methyl cyanoformate 

Downstream Products

• 1031883-58-5 C₈H₈F₃NO₅S 
• 1031883-59-6 C₂₃H₂₇NO₃Si 
• 476014-79-6 4-(tert-butyldiphenylsilyloxy)-2-ethoxypiperidine-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of (2S,4R)-4-hydroxypipecolic acid

A new synthetic route to enantiopure (2S,4R)-4-hydroxypipecolic acid from commercial ethyl (3S)-4-chloro-3-hydroxybutanoate is reported. The synthesis is based on the Pd-catalyzed methoxycarbonylation of a 4-alkoxy-substituted δ-valerolactam-derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in 20 % yield over 10 steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A stereodivergent approach to substituted 4-hydroxypiperidines

A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.