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
• Article Data: 15

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

(4aS,7aS)-6-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine is a useful reagent in the preparation of (S,?S)?-?2,?8-?diazabicyclo[4.3.0]?nonane; a moxifloxacin chiral intermediate.

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

• 706780-18-9 N-benzyl-3-Boc-aminopyrrolidin-2,5-dione 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 1076198-93-0 6-benzyl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione 
• 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 
• 87-69-4 L-Tartaric acid 
• 128740-14-7 8-benzyl-2,8-diazabicyclo[4.3.0]nonane 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 1169974-48-4 C₁₆H₁₈N₂O₃ 
• 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 

Downstream Products

• 845626-33-7 C₁₇H₂₄N₂O₂ 
• 186826-86-8 moxifloxacin hydrochloride 
• 1446655-72-6 C₃₄H₃₉N₃O₃ 
• 159991-07-8 tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate 
• 159991-06-7 (4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate 
• 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 
• 1059609-17-4 C₄₁H₄₇N₅O₅S 
• 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 
• 1028205-67-5 (S,S)-2-benzyl-8-trityl-2,8-diazabicyclo(4.3.0)nonane 
• 151213-40-0 (1S,6S)-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 
• 845626-34-8 C₁₆H₂₂N₂O 
• 845626-27-9 C₂₀H₃₂N₂O₂Si 

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.

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.

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.