163513-98-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,4S)-TERT-BUTYL 2-OXO-7-AZABICYCLO[2.2.1]HEPTANE-7-CARBOXYLATE is used as a key intermediate in the synthesis of pharmaceuticals for its unique bicyclic structure and functional groups, contributing to the development of novel therapeutic agents.
Used in Organic Chemical Reactions:
In the field of organic chemistry, (1R,4S)-TERT-BUTYL 2-OXO-7-AZABICYCLO[2.2.1]HEPTANE-7-CARBOXYLATE serves as a versatile reagent, enabling the formation of various complex organic molecules through its reactive functional groups, such as the carboxylate and the nitrogen atom within the bicyclic ring.

InChI:InChI=1/C11H17NO3/c1-11(2,3)15-10(14)12-7-4-5-8(12)9(13)6-7/h7-8H,4-6H2,1-3H3/t7-,8+/m0/s1

Upstream product

• 152533-46-5 (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 254964-19-7 (1R,4S)-2-Vinylidene-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 78293-47-7 N-<(Trifluoroacetyl)amino>cyclohex-3-ene 
• 152533-42-1 N-Benzyl-N-cyclohex-3-enyl-2,2,2-trifluoro-acetamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 154905-38-1 (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol 
• 635298-68-9 (1S,4S)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2-one 
• 636999-35-4 (1S,4S,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] 
• 449171-41-9 methyl (1S,2S,4R)-N-(tert-butoxycarbonyl)-2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 449171-42-0 (1R,2S,4R)-N-(tert-butoxycarbonyl)-2-hydroxy-1-hydroxymethyl-7-azabicyclo[2.2.1]heptane 
• 449171-43-1 (1S,4R)-N-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptan-2-one-1-carboxylic acid 

Downstream Products

• 140111-52-0 epibatidine 
• 152533-46-5 (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 152533-46-5 (±)-tert-butyl-(1SR,2RS,4RS)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 163513-99-3 (1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one 
• 152378-30-8 (-)-epibatidine 
• 152614-12-5 tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 154905-39-2 (-)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol 
• 510748-36-4 tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152885-09-1 (-)-epibatidine hydrochloride 
• 152885-09-1 (+)-epibatidine hydrochloride 

Relevant academic research and scientific papers

The enantiomers of epiboxidine and of two related analogs: Synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors

Epiboxidine hydrochlorides (+)-2 and (-)-2, which are the structural analogs of the antipodes of epibatidine (-)-1, as well as the enantiomeric pairs (+)-3/(-)-3 and (+)-4/(-)-4 were synthesized and tested for binding affinity at α4β2 and α7 nicotinic acetylcholine receptor (nAChR) subtypes. Final derivatives were prepared through the condensation of racemic N-Boc-7-azabicyclo[2.2.1]heptane-2-one (±)-5 with the resolving agent (R)-(+)-2-methyl-2-propanesulfinamide. The pharmacological analysis carried out on the three new enantiomeric pairs evidenced an overall negligible degree of enantioselectivity at both nAChRs subtypes, a result similar to that reported for both natural and unnatural epibatidine enantiomers at the same investigated receptor subtypes.

A new [4 + 2] cycloaddition strategy for the synthesis of N-acyl-7-azabicyclo[2.2.1]heptan-2-ones: A formal synthesis of (±)-epibatidine

N-Acyl-7-azabicyclo[2.2.1]heptan-2-one derivatives were prepared from N-acetyl pyrroles via a [4 + 2] cycloaddition reaction with allenes. This represents a new synthetic approach for the synthesis of epibatidine and related analogs.

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES

The present invention provides compounds of Formula A: or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a parasite, such as leishmaniasis, human African trypanosomiasis and Chagas disease.

Substituted Imidazopyridines as HDM2 Inhibitors

The present invention provides substituted imidazopyridines as described herein or a pharmaceutically acceptable salt or solvate thereof. The representative compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and potential methods of treating cancer using the same.

Tetraaza-cyclopenta[a]indenyl derivatives

The present invention provides compounds of Formula (I) as M1 receptor positive allosteric modulators for the treatment of diseases mediated by the muscarinic M1 mediator.

TETRAAZA-CYCLOPENTA[A]INDENYL DERIVATIVES

The present invention provides compounds of Formula (I) as M1 receptor positive allosteric modulators for the treatment of diseases mediated by the muscarinic M1 mediator.

Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes

We wish to report our preliminary results on the discovery and development of a catalytic, asymmetric β-hydride elimination from vinyl Pd(II)-complexes derived from enol triflates to access chiral allenes. To achieve this, we developed a class of chiral p

7-AZONIABICYCLO [2.2.1] HEPTANE DERIVATIVES, METHODS OF PRODUCTION, AND PHARMACEUTICAL USES THEREOF

Muscarinic acetylcholine receptor antagonists and methods of using them for the treatment of muscarinic acetylcholine receptor-mediated diseases, such as pulmonary diseases, are provided.

BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of GPR119 in a patient.

Synthesis of (-)-epibatidine and its derivatives from chiral allene-1,3-dicarboxylate esters

(-)-Epibatidine, an excellent candidate of non-opioidal anesthesia, was formally synthesized in short steps from di-(l)-menthyl (R)-allene-1,3- dicarboxylate that was facilely prepared as a single isomer by means of crystallization-induced asymmetric tran