134003-83-1

Basic information

• Product Name: (1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
• Synonyms: (1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
• CAS NO: 134003-83-1
• Molecular Formula: C₁₇H₂₄N₂O₂
• Molecular Weight: 288.38466
• Mol File: 134003-83-1.mol

Chemical Properties

• Boiling Point: 377.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.140±0.06 g/cm3(Predicted)
• PKA: 9.17±0.20(Predicted)
• CAS DataBase Reference: (1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(134003-83-1)
• EPA Substance Registry System: (1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(134003-83-1)

Safety Data

• Hazardous Substances Data: 134003-83-1(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
(1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as a research compound for its unique structural features and potential applications in various scientific studies. Its complex bicyclic structure and functional groups make it a valuable candidate for exploring new chemical reactions and syntheses.
Used in Industrial Processes:
(1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as an intermediate in the synthesis of other complex organic compounds, particularly in the pharmaceutical and chemical industries. Its stability and resistance to oxidation and reduction make it a suitable candidate for use in the production of various industrial chemicals and materials.
Used in Pharmaceutical Development:
(1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as a potential drug candidate in the development of new pharmaceuticals. Its unique structure and functional groups may offer novel therapeutic properties, making it a promising candidate for further investigation in the field of drug discovery and development.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 116258-17-4 (1R,4R)-5-phenylmethyl-2,5-diazabicyclo[2.2.1] heptane dihydrobromide 
• 120806-96-4 (2S,4S)-1-benzoyl-4-hydroxyproline methyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 31560-19-7 (2S,4R)-1-benzoyl-4-hydroxy-L-proline 
• 98-88-4 benzoyl chloride 
• 31560-25-5 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane 
• 61478-27-1 (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine 
• 100-46-9 benzylamine 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 134003-84-2 tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 286943-81-5 (1R,4R)-2-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane 
• 286946-75-6 tert-butyl (1R,4R)-5-(5-benzyloxy-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 

Relevant articles and documents

Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase

This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.

HDAC INHIBITORS AND USES THEREOF

Inhibitors of histone deacetylase, including compounds having a diazabicyclo[2.2.1]heptan-2-yl moiety are described together with methods for treating various disorders with such compounds.

Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)- bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds.

Substituted diazabicycloalkane derivatives

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.

DIAZABICYCLIC DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS

Compounds of formula (I) or a pharmaceutically acceptable salt thereof wherein: V is selected from the group consisting of a covalent bond and CH2; W is selected from the group consisting of a covalent bond, CH2and CH2CH2; X is selected from the group consisting of a covalent bond and CH2; Y is selected from the group consisting of a covalent bond, CH2, and CH2CH2; Z is selected from the group consisting of CH2, CH2CH2, and CH2 CH2 CH2; L1is selected from the group consisting of a covalent bond and (CH2)n; n is 1-5; R1 is selected from the group consisting of (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), and (l); R2is selected from the group consisting of hydrogen, alkoxycarbonyl, alkyl, aminoalkyl, aminocarbonylalkyl, benzyloxycarbonyl, cyanoalkyl, dihydro-3-pyridinylcarbonyl, hydroxy, hydroxyalkyl, phenoxycarbonyl, and-NH2; are useful for controlling synaptic transmission in mammal.

Diazabicyclic CNS active agents

Compounds of formula I: or pharmaceutically acceptable salts thereof, are useful for controlling synaptic transmission in mammals.

Agents for treatment of brain ischemia

A series of 5-halopyrimidin-2-ylpiperazinylalkyl derivatives having useful anti-ischemic properties for treatment and prevention of dirorders resulting from brain and/or spinal cord anoxia.