144433-70-5

Upstream product

• 59234-46-7 dimethyl (2R,6S)-piperidine-2,6-dicarboxylate 
• 501-53-1 benzyl chloroformate 
• 138-60-3 chelidamic acid 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 144433-68-1 cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine 

Downstream Products

• 144433-72-7 N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine 
• 251983-85-4 (2S,6R)-2-acetoxymethyl-6-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 
• 1451077-57-8 C₃₅H₃₁N₃O₂ 
• 144433-73-8 (2R,6S)-2-Acetoxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine-1-carboxylic acid benzyl ester 
• 177341-38-7 (2R,6S)-2-Acetoxymethyl-6-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 177473-33-5 (2R,6R)-1-Benzyl-6-methyl-piperidine-2-carbaldehyde 
• 177473-32-4 ((2R,6R)-1-Benzyl-6-methyl-piperidin-2-yl)-methanol 
• 957143-55-4 (2S,6R)-2-acetoxymethyl-6-formylpiperidine-1-carboxylic acid benzyl ester 
• 144433-71-6 N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine 

Relevant academic research and scientific papers

Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D

Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase (ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee ≥ 98%). The general method is used to effect the synthesis of (±)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.