663948-84-3

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 114676-49-2 (2S,4R)-1-benzyl-2-carbomethoxy-4-<(methylsulfonyl)oxy>pyrrolidine 
• 113451-53-9 methyl (2S,4S)-4-azido-1-benzylpyrrolidine-2-carboxylate 
• 114676-48-1 (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 142292-37-3 (2S,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol 

Downstream Products

• 1318128-96-9 tert-butyl [(3S,5R)-5-azido-1-benzylpiperidin-3-yl]carbamate 
• 1318128-99-2 tert-butyl [(3S,5S)-5-(azidomethyl)-1-benzylpyrrolidin-3-yl]carbamate 
• 1318129-38-2 tert-butyl [(3S,5R)-5-amino-1-benzylpiperidin-3-yl]carbamate 
• 1318129-41-7 tert-butyl [(3S,5S)-5-(aminomethyl)-1-benzylpyrrolidin-3-yl]carbamate 
• 1374647-16-1 tert-butyl [(3S,5R)-1-Benzyl-5-chloropiperidin-3-yl]carbamate 
• 1611481-32-3 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(2-nitrophenyl)methanone 
• 1611481-31-2 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(3-nitrophenyl)methanone 
• 1611481-30-1 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(4-nitrophenyl)methanone 
• 1611481-29-8 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(2-methoxyphenyl)methanone 
• 1611481-28-7 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(3-methoxyphenyl)methanone 
• 1611481-27-6 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(4-methoxyphenyl)methanone 
• 1611481-25-4 (S)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone 
• 849161-66-6 tert-butyl N-[(3S,5R)-5-hydroxy-3-piperidyl]carbamate 
• 1611481-19-6 tert-butyl ((3S,5R)-1-benzyl-5-hydroxypiperidin-3-yl)carbamate 

Relevant academic research and scientific papers

Enantioselective synthesis and physicochemical properties of libraries of 3-amino- and 3-amidofluoropiperidines

The enantioselective syntheses of 3-amino-5-fluoropiperidines and 3-amino-5,5-difluoropiperidines were developed using the ring enlargement of prolinols to access libraries of 3-amino- and 3-amidofluoropiperidines. The study of the physicochemical properties revealed that fluorine atom(s) decrease(s) the pKa and modulate(s) the lipophilicity of 3-aminopiperidines. The relative stereochemistry of the fluorine atoms with the amino groups at C3 on the piperidine core has a small effect on the pK a due to conformationnal modifications induced by fluorine atom(s). In the protonated forms, the C-F bond is in an axial position due to a dipole-dipole interaction between the N-H+ and C-F bonds. Predictions of the physicochemical properties using common software appeared to be limited to determine correct values of pKa and/or differences of pK a between cis- and trans-3-amino-5-fluoropiperidines.

Access to optically active 3-aminopiperidines by ring expansion of prolinols: Thermodynamic versus kinetic control

3-Aminopiperidines are of great interest because they can possess a wide range of biological activity depending on the nitrogen substituents. Different approaches their synthesis are presented and the most efficient is a ring expansion of prolinols induce

Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols

The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu4NN3) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a rat