1468-87-7

Usage

Uses

Used in Pharmaceutical Industry:
Cis-7-Azabicyclo[3.3.0]octane is used as a precursor in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs with specific therapeutic properties. Its unique structure and stereochemistry allow for the creation of molecules with targeted biological activities.
Used in Agrochemical Industry:
In the agrochemical sector, cis-7-Azabicyclo[3.3.0]octane is utilized as a starting material for the production of agrochemicals, such as pesticides and herbicides. Its structural features enable the design of effective compounds that can protect crops from pests and diseases.
Used as a Chiral Building Block in Organic Synthesis:
Cis-7-Azabicyclo[3.3.0]octane is employed as a chiral building block in organic synthesis for its potential to create enantiomerically pure compounds. This is crucial in the development of pharmaceuticals, where the stereochemistry of a molecule can significantly impact its efficacy and safety.
Used in Research and Development:
In the realm of research and development, cis-7-Azabicyclo[3.3.0]octane serves as a valuable compound for exploring new reaction pathways and mechanisms. Its unique properties make it an interesting subject for studies aimed at advancing the understanding of organic chemistry and its applications.

InChI:InChI=1/C7H13N/c1-2-6-4-8-5-7(6)3-1/h6-8H,1-5H2/t6-,7+

Upstream product

• 118989-10-9 N-benzyl-3-aza<3.3.0>bicyclooctane 
• 187329-14-2 N-chloro-3-azabicyclo[3.3.0]octane 
• 118989-06-3 N-(1'-hydroxy-2'-butyl)-3-aza-3,3,0-bicyclooctane 
• 118989-00-7 N-(1'-tert-butoxy-2'-butyl)-3-aza<3,3,0>bicyclooctane 
• 54095-53-3 cyclopent-1-ene-1,2-dicarbonitrile 
• 252662-66-1 ethyl 2-(nitromethyl)-1-cyclopentenecarboxylate 
• 5763-44-0 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione 
• 56593-76-1 hexahydrocyclopenta[c]pyrrole-1(2H)-one 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 

Downstream Products

• 54528-00-6 N-amino-aza-3-bicyclo<3.3.0>octane 
• 187329-14-2 N-chloro-3-azabicyclo[3.3.0]octane 
• 862896-23-9 N-(4-Cyanophenyl)-N-(4-hexahydrocyclopenta[c]pyrrol-2(1H)-ylbutyl)-acetamide 
• 1575815-69-8 N-(5-((hexahydrocyclopenta[c]pyrrol-2(1H)-yl)methyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide 
• 1227703-21-0 (3aR,6aS)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole 
• 54104-88-0 2-p-tolyl-octahydro-cyclopenta[c]pyrrole 
• 1205676-33-0 (3aS,6aR)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole 
• 118989-10-9 N-benzyl-3-aza<3.3.0>bicyclooctane 
• 1227703-21-0 3-azabicyclo-[3,3,0]oct-2-ene 
• 402958-25-2 (1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 926276-09-7 (3aR,6aS)-2-Boc-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 791572-14-0 (3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 

Relevant academic research and scientific papers

General formula compound of gliclazide intermediate, preparation method and application thereof

The invention relates to the field of medicine synthesis, in particular to a general formula compound of a gliclazide intermediate, a preparation method and application thereof. The invention providesa compound with a structure shown as formula I in the specification, wherein R1, R2 and R3 are H or alkyl of C1-C6 similarly or differently, and n and m are integers of 0-3 similarly or differently.The formula I compound is obtained by nitro reduction, removal of carboxyl protective group and cyclization reaction in random order, and then catalytic hydrogenation reaction is carried out to obtaina formula III compound, and the formula III compound is subjected to carbonyl reduction reaction to obtain a gliclazide intermediate with a structure shown as formula IV in the specification, whereinR1, R2 and R3 are H or alkyl of C1-C6 similarly or differently, and n and m are integers of 0-3 similarly or differently.

Preparation method of gliclazide intermediate octahydrocyclopenta[c]pyrrole

The invention discloses a preparation method of a gliclazide intermediate octahydrocyclopenta[c]pyrrole. The method comprises the following steps in order: using ethyl 2-oxaoxocyclopentanecarboxylate as the raw material to carry out condensation reaction with nitromethane, then performing hydrogenation reduction into a ring, and then conducting reduction by red aluminum so as to obtain a product. The invention adopts a brand new synthetic route, three-step reaction is carried out to prepare the gliclazide intermediate octahydrocyclopenta[c]pyrrole, the synthesis steps are effectively shortened, the total yield is greatly improved, and the cost is effectively controlled. The raw materials adopted by the method provided by the invention are all commercially available, all the steps of reaction are routine operations, also the reaction conditions are mild and easily controllable, and the production safety can be effectively improved.

Efficient catalytic hydrogenation of N-unsubstituted cyclic imides to cyclic amines

The hydrogenation of N-unsubstituted cyclic imides to the corresponding cyclic amines has been performed selectively with heterogeneous catalysts obtained from rhodium and molybdenum carbonyl precursors. Various substrates were reduced in good to high yields and selectivities. Platinum-based catalysts also proved to be efficient. Furthermore, gram-scale experiments were performed and the catalysts could be recycled.

METHOD FOR PREPARATION OF OCTAHYDROCYCLOPENTA[C]PYRROLE

The invention discloses a method for the preparation of octahydrocyclopenta[c]pyrrole, also called 3-azabicyclo[3.3.0]octane, by hydrogenation of 1,2-dicyanocyclo-1-pentene.

Study of a reduction step during the continuous synthesis of N-amino-3-azabicyclo[3.3.0]octane. Kinetics, modelling, and optimization

The reduction of N-chloro-3-azabicyclo[3.3.0]octane with sodium borohydride at different pH values and variable concentrations of the haloamine and reducing agent was studied. The reaction was found to be second order and exhibited a specific acid catalysis. The enthalpy and entropy of activation were determined at pH 12.89. A mathematical treatment of the kinetic data allowed a complete characterization of the final state and the determination of percentage of haloamine reduced as a function of temperature, [NaBH4]/ [haloamine] ratio, arid pH. A reaction mechanism is proposed.

Hypophosphorous acid-iodine: An efficient and mild reagent for cleavage of N-C bond

A mixture of hypophosphorous acid (H3PO2) and iodine in acetic acid can selectively cleave the N-alkyl bond in a variety of substituted heterocylic compounds in good to excellent yields without any damage to amide bond present in the substrates.

Kinetics of reduction of chloramines by sodium borohydride

The reduction of chloramine, methylchloramine, dimethylchloramine and N-chloro-3-azabicyclo [3.3.0]octane by sodium borohydride was studied according to pH, temperature and concentrations of haloamine and reducing agent. The interaction is bimolecular and

The Use of the β-Amino-Alcohol-N-Oxide Derivatives in the Synthesis of 2,3 or 4-Alkyl Substituted NH Pyrrolidines

Nonstabilized azomethine ylides generated from the various β-amino alcohols N-oxides 13, 17, 23 and 24 undergo cycloaddition reactions with unactivated alkenes to afford the corresponding pyrrolidines 14a-g, 18a-g, 25 und 27 in moderate to good yields.These compounds are precursors of NH pyrrolidines substituted in position 2, 3 or 4.

A 3+2 CYCLOADDITION ROUTE TO N-H PYRROLIDINES DEVOID OF ELECTRON-WITHDRAWING GROUPS

N-H pyrrolidines are obtained from intermolecular 3+2 cycloaddition reactions between nonactivated olefins and ylide generated from amine N-oxide 1 structurally designed in such a way as to allow easy dealkylation of the cycloadduct.