151213-39-7

Basic information

• Product Name: (S,S)-6-BENZYL-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE DIHYDROCHLORIDE
• Synonyms: (4aS,7aS)-6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine;(R,R)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine 2HCl;(S,S)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine 2HCl;(S,S)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine dihydrochloride/(4aS,7aS)-6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine dihydrochloride;(4AS,7aS)-6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine dihydrochloride;(4aS,7aS)-Octahydro-6-(benzyl)-1H-pyrrolo[3,4-b]pyridine;Moxifloxacin Impurity 35
• CAS NO: 151213-39-7
• Molecular Formula: C₁₄H₂₀N₂
• Molecular Weight: 289.25
• Mol File: 151213-39-7.mol

Chemical Properties

• Boiling Point: 385.4 °C at 760 mmHg
• Flash Point: 186.9 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• PKA: 10.99±0.20(Predicted)
• CAS DataBase Reference: (S,S)-6-BENZYL-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-6-BENZYL-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE DIHYDROCHLORIDE(151213-39-7)
• EPA Substance Registry System: (S,S)-6-BENZYL-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE DIHYDROCHLORIDE(151213-39-7)

Safety Data

• Hazardous Substances Data: 151213-39-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S,S)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine dihydrochloride is used as a chiral intermediate for the synthesis of moxifloxacin, an important antibiotic drug. Its unique structure and stereochemistry play a crucial role in the development of this medication, which is effective against a wide range of bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S,S)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine dihydrochloride serves as a useful reagent in the preparation of (S,S)-2,8-diazabicyclo[4.3.0]nonane. (S,S)-6-BENZYL-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE DIHYDROCHLORIDE is an essential building block for the development of various pharmaceuticals and other chemical products, highlighting the versatility of (S,S)-6-Benzyl-octahydro-pyrrolo[3,4-b]pyridine dihydrochloride in different applications.

InChI:InChI=1/C14H20N2/c1-2-5-12(6-3-1)9-16-10-13-7-4-8-15-14(13)11-16/h1-3,5-6,13-15H,4,7-11H2/t13-,14+/m0/s1

Upstream product

• 1169974-48-4 C₁₆H₁₈N₂O₃ 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 87-69-4 L-Tartaric acid 
• 128740-14-7 8-benzyl-2,8-diazabicyclo[4.3.0]nonane 
• 128740-14-7 (R,R)-8-benzyl-2,8-diazabicyclo[4.3.0]-nonane 
• 18184-75-3 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 100-46-9 benzylamine 
• 151636-46-3 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane tartrate salt 
• 151213-41-1 [1S,6R]-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane 
• 151636-47-4 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate 
• 706780-18-9 N-benzyl-3-Boc-aminopyrrolidin-2,5-dione 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 

Downstream Products

• 1059609-16-3 1a-(((4aS,7aS)-6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridin-1-yl)carbonyl)-8-cyclohexyl-N-(cyclopropylsulfonyl)-11-methoxy-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide 
• 1059609-17-4 C₄₁H₄₇N₅O₅S 
• 186826-86-8 moxifloxacin hydrochloride 
• 1059609-51-6 13-cyclohexyl-N-((dimethylamino)sulfonyl)-3-methoxy-6-((4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-1-ylcarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxamide 
• 159991-06-7 (4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate 
• 845626-34-8 C₁₆H₂₂N₂O 
• 845626-33-7 C₁₇H₂₄N₂O₂ 
• 845626-27-9 C₂₀H₃₂N₂O₂Si 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 159991-07-8 tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate 
• 1028205-67-5 (S,S)-2-benzyl-8-trityl-2,8-diazabicyclo(4.3.0)nonane 
• 845626-37-1 C₁₅H₂₂N₂ 
• 151213-46-6 [S,S]-8-benzyl-2-methyl-2,8-diazabicyclo[4.3.0]nonane 
• 1446655-72-6 C₃₄H₃₉N₃O₃ 

Relevant articles and documents

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.

A 3 - amino-pyrrolidine compound and its synthesis and use

The invention relates to 3-aminopyrrolidine compounds, and a synthetic method and uses thereof. 3-pyrrolidone compounds (compounds IIIa or IIIb) are adopted as substrates and subjected to transaminase reactions under the actions of transaminase and an amino donator to obtain the (S)-3-aminopyrrolidine compounds (compounds II). Then intramolecular cyclization and removal of amino protective groups are performed to obtain (S,S)-2,8-diazabicyclo[4,3,0] nonane (a compound I). According to the 3-aminopyrrolidine compounds, the synthetic method and the uses, a synthetic technology that is low in cost, short in process steps and environmental friendly is provided for a moxifloxacin intermediate, and the synthetic technology will have great market application value and is suitable for large-scale industrial production.

Efficient synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane

An efficient synthetic route for moxifloxacin chiral intermediate via five steps was established. First, dehydration, N-acylation, and cyclization were combined in one pot to meet the industrial requirement. Then relatively low hydrogen pressure was employed in the catalytic hydrogenation reaction with high yield. Isopropanol/water system was used in resolution, which guaranteed high yield and perfect optical purity. The racemic process conducted by manganese dioxide and Pd/C successfully converted the undesired enantiomer into the racemate and hence the total yield increased remarkably. Furthermore, mild hydrogen transfer catalytic hydrogenation method was utilized in debenzylation process instead of high-pressure hydrogenation. Total yield of 39.0% was achieved, which was much higher than that of 29.0% in literature.

Moxifloxacin intermediate compound preparation method

The invention discloses a preparation method of a moxifloxacin intermediate compound. The invention discloses a preparation method of a moxifloxacin intermediate compound represented by the formula B which is shown in the description. The preparation meth

Synthesis method for moxifloxacin side chain

The invention discloses a synthesis method for a moxifloxacin side chain.With 2,3-dipicolinic acid being a raw material, cyclization, catalytic hydrogenation, resolution and racemization are performed, and then chemical reduction and debenzylation are performed to obtain moxifloxacin side chain.Resolution, racemization and chemical reduction are performed in sequence, sodium borohydride is used for replacing high-risk lithium aluminum hydride to synthesize the moxifloxacin side chain, and the synthesis method has the advantages that industrial waste materials are reduced, the production cost is lowered, and productivity is increased.

(S, S) - 2,8-diazabicyclo [4, 3, 0] nonane synthetic method

The invention discloses a preparation method of a compound 1 (S,S)-2,8-diazabicyclo[4.3.0]nonane. With existing methods, chiral separations are carried out in the last process, and chiral control are not realized in pre-stage main ring synthesis process, such that a final total yield is substantially low, and synthesizing cost of (S,S)-2,8-diazabicyclo[4.3.0]nonane is severely influenced. According to the method provided by the invention, in an organic solvent, under the existence of organic amine and under a temperature of 0-30 DEG C, benzenesulfonamide is subjected to a reaction with acrolein, such that a compound 5 is prepared; under the existence of organic amine and a chiral catalyst, the compound 5 is subjected to a D-A addition reaction with a compound 4, such that a compound 6 is prepared; the compound 6 is processed through catalytic hydrogenation and carbonyl reduction; and protective group removing and chiral separation purification are carried out under an acidic condition. With the method provided by the invention, a problem of low total yield of finished product caused by chiral separation of prior arts is completely solved, and product yield is improved.

METHOD FOR PRODUCTION OF (S,S)-6-BENZYLOCTAHYDRO-1H-PYRROLO[3,4-B]PYRIDINE, AN INTERMEDIATE OF AZABICYCLO PYRIDINE DERIVATIVES

The present invention relates to a cost effective process for the production of (S,S)-6- benzyloctahydro-1H-pyrrolo[3,4-b]pyridine of Formula (I), an important intermediate for the manufacture of azabicyclo pyridine derivatives.

IR, FT-ICR-MS studies on (1′S, 6′S)-1-cyclopropyl-7-(2,8- diazabicyclo[4.3.0] non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid hydrochloride salt

The infrared spectra of (1′S, 6′S)-1-cyclopropyl-7-(2,8- diazabicyclo[4.3.0] non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid hydrochloride salt (CLF-HCl) were studied and compared with free base. Their fragmentation pathways were investigated using tandem mass spectrometric (MS/MS) techniques on Fourier-transform ion cyclotron resonance spectrum, and many characteristic fragment ions were found.

A novel synthesis of (4aS,7aS)-Octahydro-1H-pyrrolo[3,4-b]pyridine:An intermediate of Moxifloxacin Hydrochloride

A novel synthesis of (4aS, 7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine (1) is demonstrated alongwith recovery and reuse of chiral auxiliary naproxen. Further to this alternative stereoselective reduction procedures on 6-benzyl-5H- pyrrolo[3,4-b]pyridine-5,7(6H)-dione 3 enabling the desired chirality in the nonane 1 is demonstrated.

SYNTHESIS OF (4aS,7aS)-OCTAHYDRO-1H-PYRROLO[3,4-b]PYRIDINE

The present invention relates to the stereoselective synthesis of (4aS,7aS)-octahydro-1H-pyrrolo [3, 4-b]pyridine, as well as the conversion thereof, to give Moxifloxacin. Particularly, the present invention relates to a method for the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) comprising : (a) the optical resolution by enzymatic hydrolysis of the intermediate dialkyl-1-alkylcarbonylpiperidine-2,3-dicarboxylate racemate of formula (II) to give, following isolation, the intermediate dialkyl-(2S,3R)-1-alkylcarbonyl-piperidine-2,3-dicarboxylate of formula (III) in which AIk is a straight or branched C1-C5 alkyl group; (b) the conversion of the intermediate (III) to (4aR,7aS)-1-alkylcarbonylhexahydrofuro[3, 4-b]pyridine-5,7-dione of formula (IV) in which AIk has the meanings set forth above; (c) the conversion of the intermediate (IV) to (4aS,7as)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) with an optical purity above 99%.