158060-81-2

Basic information

• Product Name: trans-octahydro-1H-pyrrolo[3,4-b]pyridine
• Synonyms: trans-octahydro-1H-pyrrolo[3,4-b]pyridine;(4aS,7aR)-Octahydro-1H-pyrrolo[3,4-b]pyridine;Moxifloxacin Related Impurity 1;TRANS-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE;(4aR,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine
• CAS NO: 158060-81-2
• Molecular Formula: C7H14N2
• Molecular Weight: 126.19946
• Mol File: 158060-81-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: trans-octahydro-1H-pyrrolo[3,4-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-octahydro-1H-pyrrolo[3,4-b]pyridine(158060-81-2)
• EPA Substance Registry System: trans-octahydro-1H-pyrrolo[3,4-b]pyridine(158060-81-2)

Safety Data

• Hazardous Substances Data: 158060-81-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-octahydro-1H-pyrrolo[3,4-b]pyridine is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly in the preparation of quinoline-derivative antibiotics. Its unique structure allows for the development of new drugs with potential applications in treating bacterial infections.
Used in Chemical Synthesis:
Trans-octahydro-1H-pyrrolo[3,4-b]pyridine is used as a building block in the chemical synthesis of various organic compounds. Its reactivity and structural features make it a valuable component in the creation of complex molecules for a range of applications, including the development of new materials and pharmaceuticals.
Used in Quality Control:
As an impurity in the production of Moxifloxacin (M745000), a fluorinated quinolone antibacterial, trans-octahydro-1H-pyrrolo[3,4-b]pyridine plays a role in quality control and assurance processes. Monitoring and controlling the presence of this impurity ensures the safety, efficacy, and purity of the final pharmaceutical product.

Upstream product

• 151213-39-7 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate 
• 1253122-67-6 (1S,6R)-cis-8-((S)-1-phenylethyl)-2,8-diazabicyclo[4.3.0]nonane 
• 1427038-03-6 C₂₂H₂₄N₂O₅ 
• 1009051-59-5 (4R)-1,6-dioxo-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2, 1-c][1,4]oxazine-9-carboxylic acid methyl ester 
• 1427038-01-4 [4R-4α,9β,9aα]-1,6-dioxo-4-phenyloctahydropyrido[2,1-c][1,4]oxazine-9-carboxylic acid methyl ester 
• 1427038-02-5 (2R,3S)-methyl 2-(benzylcarbamoyl)-1-((R)-2-hydroxy-1-phenylethyl)-6-oxopiperidine-3-carboxylate 
• 64-04-0 phenethylamine 
• 128740-14-7 8-benzyl-2,8-diazabicyclo[4.3.0]nonane 
• 1430075-11-8 1-benzyl-4-(3-ethoxycarbonylpropyl)-3-pyrrolidone 
• 1430075-01-6 C₂₄H₃₂N₂O₂ 
• 1430075-04-9 C₂₂H₃₀N₂O 
• 1430075-02-7 (5S,6S)-2-((R)-1-phenyl-ethyl)-8-benzyl-3-oxo-2,8-diazabicyclo[4.3.0]nonane 
• 1430075-03-8 (4aS,7aS)-6-benzyl-1-((R)-1-phenylethyl)octahydro-1H-pyrrolo[3,4-b]pyridine 
• 1430075-05-0 C₂₉H₃₄N₂O₂ 

Downstream Products

• 151096-44-5 1-cyclopropyl-6,8-difluoro-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 721970-37-2 N-methylmoxifloxacin 
• 186826-86-8 moxifloxacin hydrochloride 
• 151213-39-7 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate 
• 151636-46-3 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane tartrate salt 
• 195532-12-8 8-Cyano-1-cyclopropyl-7-((1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 721970-35-0 methyl 1-cyclopropyl-6-fluoro-8-methoxy-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 1029364-75-7 1-cyclopropyl-8-ethoxy-6-fluoro-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4 oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 721970-36-1 1-cyclopropyl-7-{(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl}-6-fluoro-8-hydroxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 151096-09-2 moxifloxacin 
• 151096-44-5 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 158060-81-2 2,8-diazabicyclo[4.3.0]nonane 

Relevant articles and documents

Method for preparing moxifloxacin intermediate (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane

The invention provides a method for preparing a moxifloxacin intermediate (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane, and relates to the technical field of organic synthesis. According to the present invention, the 2-chloromethyl methyl nicotinate is subjected to asymmetric hydrogenation catalysis so as to obtain the intermediate with high chiral purity, chiral resolution is not required, and the moxifloxacin intermediate (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane can be obtained through ammonolysis, reduction and cyclization. According to the method provided by the invention, chiral resolution is not needed, the process is simple, the process steps are short, the cost is low, and the product is high in chiral purity and high in total yield.

Method for preparing moxifloxacin intermediate (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane

The invention provides a method for preparing a moxifloxacin intermediate (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane, and relates to the technical field of organic synthesis. According to the method, the azaphthalide is used as a raw material, and due to the ring structure of the azaphthalide, the other two non-corresponding chiral isomers which are not needed in chiral reduction are almost not generated; the chiral purity of the intermediate obtained through reduction is very high, resolution is not needed, and (S, S)-2, 8-diazabicyclo [4, 3, 0] nonane can be obtained directly through ammonolysis, reduction, chlorination and cyclization subsequently. According to the method provided by the invention, chiral resolution is not needed, the process is simple, the process steps are short, the cost is low, and the product is high in chiral purity and high in total yield. Furthermore, in the subsequent product salifying and refining step, carboxylic acid with a chiral structure does not need to be used for salifying, and common achiral carboxylic acid can be used for refining, so the product purity is further improved.

(S, S)-2, 8-diazabicyclo[4.3.0]nonane intermediate, and preparation method and application thereof

The invention discloses a (S, S)-2, 8-diazabicyclo[4.3.0]nonane intermediate, and a preparation method and application thereof. New compounds, namely compounds II-V, are taken as key intermediates, a new route for synthesizing (S, S)-2, 8-diazabicyclo[4.3.0]nonane is developed, and in the route, dialkoxy acetate taken as an initial raw material in the route sequentially undergoes Claisen condensation, substitution reaction, intramolecular dehydration cyclization, catalytic hydrogenation reduction, chiral resolution, dissociation, hydrolysis, intramolecular dehydration cyclization and catalytic hydrogenation to obtain the(S, S)-2, 8-diazabicyclo[4.3.0]nonane. The preparation method is simple, the total reaction yield is high, the product quality is good, the process route is green and environment-friendly, and the method has a good industrial application prospect.

Preparation method of intermediate

The invention relates to a preparation method of an intermediate, and belongs to the field of medicinal chemistry. The preparation method comprises at least one reaction step of an addition elimination reaction, a cyclization reaction, a reduction reaction, a decarboxylation reaction and a hydrogenation reaction. According to the method disclosed by the invention, the target intermediate with a single configuration can be simply and conveniently obtained, chiral resolution is effectively avoided, the yield is improved, the cost is reduced, and industrial production is facilitated.

Preparation method of moxifloxacin intermediate

The invention discloses a preparation method of a moxifloxacin intermediate. The invention provides a preparation method of a compound as shown in a formula III, which comprises the following step: ina solvent, in the presence of alkali, carrying out cyclization reaction as shown in the specification on a compound as shown in a formula II to obtain the compound as shown in the formula III. The method is simple to operate, high in chiral selectivity, simple in process, high in yield and high in purity.

New moxifloxacin impurity and preparation method and use thereof

The invention provides a new moxifloxacin impurity and provides a preparation method and use as an impurity control of the new impurity. A commercially available bulk simple chemical is used as a starting material to construct a chiral dual ring, and further an impurity compound is synthesized; the reaction process has no need of chiral resolution; in addition, the operation is simple, the reaction condition is mild, and the application prospect is good. The moxifloxacin prepared by the invention has high impurity purity, and effectively ensures the purity of the impurity control and the accuracy of analysis work.

Method for synthesizing moxifloxacin and derivatives thereof

The invention provides a method for synthesizing moxifloxacin and derivatives thereof. Aminopyrrolidone derivatives are constructed to further obtain (S,S)-2,8-diazo-bicyclo[4.3.0]nonane so as to synthesize the moxifloxacin and the derivatives thereof. The method has the beneficial effects that raw materials are wide in source and low in price; chiral resolution is not needed in a preparation process; the yield and purity are relatively high; the process cost is further reduced; obvious economic value is achieved.

Synthetic method for moxifloxacin chiral side chain intermediate

The invention provides a synthetic method for a moxifloxacin chiral side chain intermediate. The method provided by the invention uses an easily-available and inexpensive L-asparagine as a starting material to obtain the moxifloxacin chiral side chain intermediate through an eight-step reaction; and the whole route has novel design and avoids a chiral separation process adopted by most routes, andthe method has higher practicability, a high yield, a quick reaction speed and few by-products, and is very suitable for industrial application.

Asymmetric synthesis method for (S,S)-2,8-diazabicyclo[4,3,0]nonane

The invention relates to an asymmetric synthesis method for (S,S)-2,8-diazabicyclo[4,3,0]nonane. N-benzyl-butene imidodicarbonic diamide is taken as a raw material, in presence of a chiral squaramidecatalyst (III), the N-benzyl-butene imidodicarbonic diamide and N-para-toluene sulfonyl-N'-propylene imidogen hydrazine (II) are subjected to an asymmetric [2+4] addition reaction, and 8-benzyl-2-para-toluene sulfonamide-7,9-dioxo-(1S,6R)-2,8-diazabicyclo[4,3,0]-3-alkene nonane is obtained; through the steps of recrystallization, reduction, acid-catalyzed hydrolysis and reduction, the (S,S)-2,8-diazabicyclo[4,3,0]nonane is obtained. The synthesis method is simple, the yield of the asymmetric catalysis product is high, the enantioselectivity of the product through recrystallization can reach 90% or above, and the asymmetric synthesis method is mild in condition, simple to implement, low in production cost and capable of being used for industrialized production.

Method for synthesizing (S,S)-2,8-diazabicyclo[4.3.0]nonane

The invention discloses a method for synthesizing (S,S)-2,8-diazabicyclo[4.3.0]nonane. The method comprises the following steps of: (a) adopting a compound which is shown in a formula V and comprisesa chiral auxiliary group and an amino protecting group as a raw material, and performing an intramolecular cyclization reaction to obtain a compound shown in a formula VI; (b) removing the chiral auxiliary group and amino protecting group from the compound shown in the formula V so as to obtain a compound shown in a formula VII, wherein when X is a hydrogen atom, the compound shown in the formulaVII is (S,S)-2,8-diazabicyclo[4.3.0]nonane; and (c) when X is an oxygen atom, performing a reduction reaction on the compound shown in the formula VII by using amide so as to obtain (S,S)-2 ,8-diazabicyclo[4.3.0]nonane.