370882-99-8

Basic information

• Product Name: (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane
• Synonyms: (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane;tert-Butyl (1R,6S)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate;(1R,6S)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester
• CAS NO: 370882-99-8
• Molecular Formula: C₁₁H₂₀N₂O₂
• Molecular Weight: 212.2887
• Mol File: 370882-99-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane(370882-99-8)
• EPA Substance Registry System: (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane(370882-99-8)

Safety Data

• Hazardous Substances Data: 370882-99-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane is utilized as a chiral building block for the synthesis of enantiopure compounds. Its unique structure and the Boc protecting group allow for the creation of molecules with specific stereochemistry, which is essential in pharmaceuticals and agrochemicals where the biological activity of a compound can be highly dependent on its stereochemistry.
Used in Asymmetric Catalysis:
In the field of catalysis, (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane is studied for its potential as a catalyst in organic reactions. Its chiral nature and the Boc group's influence on reactivity make it a candidate for facilitating asymmetric transformations, which are vital for producing enantioselective products that are often required in the synthesis of biologically active molecules.
Used in Pharmaceutical Industry:
(1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane is employed in the pharmaceutical industry as a key intermediate in the synthesis of chiral drugs. The ability to produce enantiomerically pure compounds is critical for ensuring the desired therapeutic effects and minimizing potential side effects associated with the less active enantiomer.
Used in Agrochemical Industry:
Similarly, in agrochemicals, (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane serves as a precursor for the development of enantioselective pesticides and herbicides. The production of pure enantiomers can lead to more effective and environmentally friendly agrochemicals by reducing the amount of inactive enantiomer that needs to be applied.

Upstream product

• 1295522-56-3 (1R,6S)-tert-butyl 8-((S)-1-phenylethyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate 
• 923956-65-4 (1R,6S)-8[(1R)-1-phenyl-ethyl]-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester 
• 370882-98-7 (1R,6S)-8-(2-nitrobenzenesulfonyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester 

Downstream Products

• 370883-00-4 tert-butyl (1R,6S)-8-(6-chloro-5-methyl-3-pyridinyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate 
• 1295522-42-7 (1R,6S)-tert-butyl 8-(6-methylpyridin-2-yl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate 

Relevant articles and documents

FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS

Disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS

Certain disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane are described, which are useful as orexin inhibitors. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

Synthesis and structure-activity relationships of 3,8-diazabicyclo[4.2.0] octane ligands, potent nicotinic acetylcholine receptor agonists

A series of potent neuronal nicotinic acetylcholine receptor (nAChR) ligands based on a 3,8-diazabicyclo-[4.2.0]octane core have been synthesized and evaluated for affinity and agonist efficacy at the human high affinity nicotine recognition site (hα4β2) and in a rat model of persistent nociceptive pain (formalin model). Numerous analogs in this series exhibit picomolar affinity in radioligand binding assays and nanomolar agonist potency in functional assays, placing them among the most potent nAChR ligands known for the hα4β2 receptor. Several of the compounds reported in this study (i.e., 24, 25, 28, 30, 32, and 47) exhibit equivalent or greater affinity for the hα4β2 receptor relative to epibatidine, and like epibatidine, many exhibit robust analgesic efficacy in the rat formalin model of persistent pain.

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 central nervous system active agents

Compounds of formula I pharmaceutical compositions of these compounds, and use of said compositions to control synaptic transmission in mammals.