54528-00-6

Basic information

• Product Name: 3-Amino-3-azabicyclo[3.3.0]octane
• Synonyms: N-AMINO-3-AZA-BICYCLO[3,3,0]OCTANE HYDROCHLORIDE;N-AMINO-3-AZABYCICLO(3,3,0)-OCTANE HYDROCHLORIDE;TIMTEC-BB SBB003933;hexahydrocyclopenta[c]pyrrol-2(1H)-amine;N-Amino-3-Azabicyclo(3,3,0)Octane Hcl;3-Amino-3-Azabicyclo[3.3.0]Octane HCl;N-AMINO-AZA-3-BICYCLO[3,3,0]OCTANE HYDROCHLORIDE;N-amino-aza-3-bicyclo[3,3,0]octaneHCl-
• CAS NO: 54528-00-6
• Molecular Formula: C₇H₁₄N₂
• Molecular Weight: 126.2
• EINECS: 259-201-9
• Mol File: 54528-00-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 187.975 °C at 760 mmHg
• Flash Point: 73.159 °C
• Appearance: /
• Density: 1.038 g/cm³
• Vapor Pressure: 0.613mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C
• PKA: 8.19±0.20(Predicted)
• CAS DataBase Reference: 3-Amino-3-azabicyclo[3.3.0]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-3-azabicyclo[3.3.0]octane(54528-00-6)
• EPA Substance Registry System: 3-Amino-3-azabicyclo[3.3.0]octane(54528-00-6)

Safety Data

• Hazardous Substances Data: 54528-00-6(Hazardous Substances Data)

Usage

Uses

Gliclazide intermediate

InChI:InChI=1/C7H14N2/c8-9-4-6-2-1-3-7(6)5-9/h6-7H,1-5,8H2

Upstream product

• 1468-87-7 octahydrocyclopenta[c]pyrrole 
• 54786-86-6 2-nitroso-octahydrocyclopenta[c]pyrrole 
• 1050666-51-7 N-amino-1,2-cyclopentanedicarboximide 

Downstream Products

• 1103532-92-8 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1H-pyrazole-4-carboxamide 
• 1020106-12-0 1-(2,4-dichlorophenyl)-4-methyl-5-[((E)-5-pent-1-enyl)thiophen-2-yl]-1H-pyrazole-3-carboxylic acid (hexahydrocyclopenta[c]pyrrol-2-yl)amide 
• 1058164-50-3 1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-5-(5-pentylthiophen-2-yl)-1H-pyrazole-3-carboxamide 
• 1058164-52-5 5-(5-(but-1-ynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1058164-54-7 1-(2,4-dichlorophenyl)-5-(5-(hex-1-ynyl)thiophen-2-yl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1058164-60-5 1-(2,4-dichlorophenyl)-5-(5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1058164-61-6 5-(5-(cyclopropylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1020106-18-6 5-(5-(cyclopentylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1020106-19-7 5-(5-(cyclohexylethynyl)thiophen-2-yl)-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1058164-42-3 1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-5-(5-(pent-1-ynyl)thiophen-2-yl)-1H-pyrazole-3-carboxamide 
• 1160842-65-8 C₂₂H₂₁Cl₃N₄OS 
• 58108-05-7 3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride 
• 21187-98-4 gliclazide 
• 25771-21-5 N,N-dimethyl 4-(trifluoromethyl)benzamide 

Relevant articles and documents

Kinetic characterization of a transient reaction by degeneration of the precursor mechanism: Application to the synthesis of 3,4-diazabicyclo[4.3.0]non- 2-ene

The rate of the oxidation of N-amino-3-azabicyclo[3.3.0]octane by chloramine has been studied by GC and HPLC between pH 10.5 and 13.5. The second-order reaction exhibits specific acid catalysis. The formation of N,N′-azo-3-azabicyclo(3.3.0)octane or 3,4-diazabicyclo(4.3.0)non-2-ene is pH, concentration, and temperature dependent. In alkaline media, the exclusive formation of 3,4-diazabicyclo[4.3,0]non-2-ene is observed. Kinetic studies show that the oxidation of N-amino-3-azabicyclo[3.3.0]octane by chloramine is a multi-step process with the initial formation of a diazene-type intermediate, which is converted by hydroxide ions into 3,4-diazabicyclo[4.3.0]non-2-ene. Because it was not possible to follow the rate of change of the intermediate concentration, to determine the kinetics of 3,4diazabicyclo[4.3.0]non-2-ene formation, a procedure based on the degeneration of the precursor process was adopted. An appropriate mathematical treatment allowed a quantitative interpretation of all the phenomena observed over the given pH interval. The activation parameters were determined.

Synthesis and NMR investigation of 3,4-diazabicyclo[4.3.0]non-2-ene and N,N'-azo-3-azabicyclo[3.3.0]octane. X-ray crystal structure analysis of a new tetrazene derivative

3,4-Diazabicyclo[4.3.0]non-2-ene and N,N'-azo-3-azabicyclo[3.3.0]octane are the main products of the oxidation of N-amino-3-azabicyclo[3.3.0]octane by chloramine. These new compounds have been isolated and characterized. A structural study has been performed with the goal of establishing the cis- trans configuration at the bicyclic junction. Multinuclear proton decoupling carried out on the endocyclic hydrazone has allowed the determination of the coupling constant of the bridgehead hydrogens. A low temperature conformational study shows splitting of the 13C signal of the carbon atom located α with respect to the ammonia nitrogen. This result, consistent with a cis structure, was confirmed by a nmr analysis conducted on the solid tetrazene derivative. The X-ray data collection on a single crystal of the tetrazene has permitted us to determine the crystallographic properties of this compound. Data processing by direct methods reveals that the geometry of the molecule presents a cis configuration for the bicyclic bridge link and a trans one for the azo group, confirming thus the main results obtained by nmr studies.

Preparation method of gliclazide side chain and preparation method of gliclazide

The invention relates to a preparation method of N-amino-3-azabicyalo [3.3.0] octane serving as a gliclazide side chain. The gliclazide side chain is obtained by carrying out one-step hydrogenation reduction on N-cyclopentyl amine imide through a transition metal atom-modified ruthenium-carbon catalyst. The activity of the modified ruthenium-carbon catalyst used in the method is obviously higher than that of an existing commercial ruthenium-carbon catalyst, so that the imide hydrogenation reaction which is hard to realize in the N-cyclopentyl amine imide can be carried out successfully. The preparation method of the gliclazide side chain is safe, efficient, high in yield and simple for posttreatment; the catalyst can be cyclically used indiscriminately, so that the production cost is substantially reduced, and green synthesis is basically realized; no waste water and no waste slag are produced; and the preparation method is particularly suitable for large-scale industrial production. The invention further relates to a production method of gliclazide, which has the advantages of short synthesis path, high yield, low preparation cost and the like.

New method for preparing gliclazide intermediate

The invention discloses a new method for preparing a gliclazide intermediate, and particularly relates to a preparation method for a blood sugar lowering medicine gliclazide intermediate 2-amino octahydrocyclopenta[c]pyrrole. The method sequentially includes the following steps that octahydrocyclopenta[c]pyrrole is adopted as a raw material, and the product is obtained sequentially through nitrosation and a reduction reaction. Conditions of a brand-new reduction reaction are provided, the raw material for use is wide and sufficient in source, the price is low, the reaction condition is mild, the process is simple, all steps of the reaction are conventional operation, and the production cost is reduced.