1363378-08-8

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl(3R,5S)-5-fluoropiperidin-3-ylcarbamate is used as a precursor or intermediate for the synthesis of pharmaceutical drugs. Its unique structure and properties contribute to the development of new medications, enhancing the therapeutic potential of existing drugs and facilitating the creation of novel therapeutic agents.
Safety Considerations:
When working with tert-butyl(3R,5S)-5-fluoropiperidin-3-ylcarbamate in a laboratory setting, it is crucial to handle this chemical with care and adhere to safety protocols. Proper handling and safety measures ensure the protection of researchers and the environment, minimizing potential risks associated with chemical exposure.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1611480-83-1 (2R,4R)-methyl 4-azido-1-tritylpyrrolidine-2-carboxylate 
• 1611480-95-5 tert-butyl (3R,5S)-5-fluoro-1-tritylpiperidin-3-ylcarbamate 

Downstream Products

• 1611480-99-9 ((3R,5S)-3-amino-5-fluoropiperidin-1-yl)(phenyl)methanone 

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.