907544-20-1

Basic information

• Product Name: tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate
• Synonyms: tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate;Cis-(3S,4R)-1-Boc-4-amino-3-fluoropiperidine;Cis (3s, 4r)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate
• CAS NO: 907544-20-1
• Molecular Formula: C₁₀H₁₉FN₂O₂
• Molecular Weight: 218.2684632
• Mol File: 907544-20-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 285.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.88±0.40(Predicted)
• CAS DataBase Reference: tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate(907544-20-1)
• EPA Substance Registry System: tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate(907544-20-1)

Safety Data

• Hazardous Substances Data: 907544-20-1(Hazardous Substances Data)

Usage

General Description

Tert-butyl (3S,4R)-4-amino-3-fluoropiperidine-1-carboxylate is a complex organic molecule with specific stereochemistry. It belongs to the compound class of piperidines which are heterocyclic organic compounds. The presence of the tert-butyl group, fluorine atom and carboxylate group grant it unique reactivity and properties, enabling it to perform a broad range of chemical reactions. Its unique structure could make it particularly useful in the synthesis of pharmaceutical drugs, agrochemicals or other materials where specific 3-dimensional structures are important. However, as with many complex organic molecules, the specific characteristics, potential applications and safety aspects are heavily determined by its precise structural form and these would need to be studied in detail for each specific use.

Upstream product

• 907572-24-1 tert-butyl (3S,4R)-4-(benzylamino)-3-fluoro-piperidine-1-carboxylate 
• 211108-52-0 (±)-cis-4-benzylamino-3-fluoropiperidine-1-carboxylic acid tert-butyl ester 
• 211108-50-8 tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 211108-48-4 tert-butyl 4-[(trimethylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate 

Downstream Products

• 1033748-75-2 (3S,4R)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-fluoropiperidine-1-carboxylate 
• 1034057-93-6 benzyl ((3S,4R)-3-fluoropiperidin-4-yl)carbamate hydrochloride 
• 1033748-74-1 benzyl (3S,4R)-1-[(2-tert-butyldimethylsilyloxy)ethyl]-3-fluoropiperidin-4-ylcarbamate 

Relevant articles and documents

Synthesis of a CGRP Receptor Antagonist via an Asymmetric Synthesis of 3-Fluoro-4-aminopiperidine

A practical and efficient enantioselective synthesis of the calcitonin gene-related peptide receptor antagonist 1 has been developed. The key structural component of the active pharmaceutical ingredient is a syn-1,2-amino-fluoropiperidine 4. Two approaches were developed to synthesize this important pharmacophore. Initially, Ru-catalyzed asymmetric hydrogenation of fluoride-substituted enamide 8 enabled the synthesis of sufficient quantities of compound 1 to support early preclinical studies. Subsequently, a novel, cost-effective route to this intermediate was developed utilizing a dynamic kinetic asymmetric transamination of ketone 9. This synthesis also features a robust Ullmann coupling to install a bis-aryl ether using a soluble Cu(I) catalyst. Finally, an enzymatic desymmetrization of meso-diester 7 was exploited for the construction of the γ-lactam moiety in 1.

Optimization of pyrrolamide topoisomerase II inhibitors toward identification of an antibacterial clinical candidate (AZD5099)

AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

CONDENSED PYRIDINE COMPOUND

The present invention provides a compound having excellent JAK3 inhibitory activity and being useful as an active ingredient of an agent for treating and/or preventing various immune diseases including autoimmune diseases, inflammatory diseases, and allergic diseases. As a result of investigations with respect to novel condensed heterocyclic derivatives, the inventors have verified that a condensed pyridine compound has excellent JAK3 inhibitory activity, thereby completing the present invention. More specifically, it has been verified that since the compound according to the present invention has inhibitory activity against JAK3, the compound is useful as an active ingredient of an agent for treating or preventing diseases caused by undesirable cytokine signal transduction (e.g., rejection during live organ/tissue transplantation, autoimmune diseases, asthma, atopic dermatitis, rheumatism, psoriasis and atherosclerotic disease), or diseases caused by abnormal cytokine signal transduction (e.g., cancer and leukemia).