151213-41-1

Basic information

• Product Name: 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)-
• Synonyms: cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane;(1S,6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane;cis-8-Benzyl-7,9-dioxo-2,8-diazabicyclo(4.3.0)nonan;6-benzylte-(4aS,7aRdes)-trahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione;(4aR,7aS)-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione
• CAS NO: 151213-41-1
• Molecular Formula: C14H16N2O2
• Molecular Weight: 244.293
• Mol File: 151213-41-1.mol

Chemical Properties

• Boiling Point: 468.5±45.0 °C(Predicted)
• Density: 1.227±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)-(151213-41-1)
• EPA Substance Registry System: 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)-(151213-41-1)

Safety Data

• Hazardous Substances Data: 151213-41-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)is used as a chiral intermediate for the synthesis of various pharmaceutical compounds. Its unique molecular structure and stereochemistry make it a valuable building block in the development of new drugs with improved efficacy and selectivity.
2. Used in Chemical Synthesis:
In the field of organic chemistry, 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)can be employed as a versatile reagent for the preparation of a wide range of chemical products. Its reactive functional groups and specific stereochemistry allow for selective reactions and the formation of complex molecular architectures.
3. Used in Research and Development:
Due to its unique structure and potential applications, 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)is also used in research and development settings. Scientists and chemists can explore its properties, reactivity, and potential applications in various fields, such as materials science, drug discovery, and chemical engineering.
4. Used in Drug Delivery Systems:
Similar to gallotannin, 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione, tetrahydro-6-(phenylmethyl)-, (4aS-cis)may also be utilized in the development of novel drug delivery systems. Its unique structure could be exploited to improve the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical compounds, particularly in the context of targeted drug delivery and controlled release applications.

Upstream product

• 7760-07-8 D-gluconic acid 
• 706780-18-9 N-benzyl-3-Boc-aminopyrrolidin-2,5-dione 
• 1076198-93-0 6-benzyl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 16308-68-2 allyl phenyl carbonate 
• 18184-75-3 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 151434-04-7 (4aR,7aS)-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione mono D-(-)-tartarate 
• 100-46-9 benzylamine 

Downstream Products

• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 151213-39-7 (S,S)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane-D-tartrate 

Relevant articles and documents

Convenient enzymatic resolution of cis-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione using lipase to prepare the intermediate of moxifloxacin

A convenient and efficient route has been successfully developed for preparing (4aR,7aS)-6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione through enzyme-mediated kinetic resolution processes under mild and environmentally acceptable conditio

Preparation method of compound A

The invention discloses a preparation method of a compound A. The compound A is (S,R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane, and the preparation method comprises the following steps: salifying and crystallizing a hydrogenation product and a resolving agent to obtain a resolution salt, and extracting a resolution product (S,R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane through alkali treatment. The process is simple to operate, and the single resolution yield is greater than 40%; and the chiral purity ee value is greater than 98%, and the method has high industrial production value.

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.

Preparation method of iridium catalyzed moxifloxacin side chain intermediate

The invention discloses a preparation method of an iridium catalyzed moxifloxacin side chain intermediate. The preparation method of the iridium catalyzed moxifloxacin side chain intermediate comprises the following step: under the catalysis of a chiral c

Preparation method of moxifloxacin side chain intermediate with rhodium catalysis

The invention discloses a preparation method of a moxifloxacin side chain intermediate with rhodium catalysis. The method includes steps of: under effect of a chiral catalyst, performing an asymmetrichydrogenation reaction to 6-benzyl-1,2,3,4-tetrahydro-p

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.

Design, Synthesis, Antifungal Activities and SARs of (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic Acid Derivatives

Based on the structure of natural product 2-aryl-4,5-dihydrothiazole-4-carboxylic acid, a series of novel (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The single crystal structure of compound 9b was determined by X-ray diffraction analysis. The antifungal activities were evaluated for the first time. The bioassay results indicated that most compounds exhibited moderate to good antifungal activities. The antifungal activities of compound 13a (against Cercospora arachidicola Hori), 13d (against Alternaria solani), and 16e (against Cercospora arachidicola Hori) were 61.9%, 67.3% and 61.9%, respectively, which are higher than those of the commercial fungicides chlorothalonil and carbendazim. Moreover, compound 13d exhibited excellent antifungal activities against 7 kinds of the fungi tested (66.7%, 77.3%, 63.0%, 87.9%, 70.0%, 70.0% and 80.0% at 50 μg?mL). Therefore, 13d can be used as a new lead structure for the development of antifungal agents.

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.

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.

Highly efficient racemisation of a key intermediate of the antibiotic moxifloxacin

N-Chlorination by sodium dichloroisocyanurate and dehydrochlorination by TEA, followed by hydrogenation, allowed (1R,6S)-8-benzyl-7,9-dioxo-2,8- diazabicyclo[4.3.0]nonane to be quantitatively racemised and the resulting trans-free cis racemate to be recycled into the resolution process to yield (1S,6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane, a key intermediate of moxifloxacin.