597569-42-1

Basic information

• Product Name: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER
• Synonyms: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER;(1S,3aR,6aS)-Hexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid 2-(tert-butyl) ester;HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID;(1S,3aR,6aS)-2-(tert-Butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
• CAS NO: 597569-42-1
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 253.29426
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 597569-42-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 386.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.196
• Storage Temp.: 2-8°C
• PKA: 4.05±0.20(Predicted)
• CAS DataBase Reference: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER(597569-42-1)
• EPA Substance Registry System: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER(597569-42-1)

Safety Data

• Hazardous Substances Data: 597569-42-1(Hazardous Substances Data)

Usage

Description

HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER is a white solid compound with a complex chemical structure. It is characterized by its hexahydro-cyclopenta[c]pyrrole framework and a 2-tert-butyl ester group, which contributes to its unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER is used as a key intermediate in the synthesis of peptidomimetic protease inhibitors. These inhibitors play a crucial role in the development of novel drugs targeting various diseases, including viral infections and cancer, by mimicking the structure of natural peptides and blocking the action of specific proteases.
Used in Chemical Research:
As a complex organic molecule, HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER can also be utilized in chemical research for understanding the reactivity and properties of similar compounds. This knowledge can be applied to the design and synthesis of new molecules with potential applications in various industries, such as materials science, pharmaceuticals, and agrochemicals.
Used in Material Science:
The unique structural features of HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER may also find applications in the development of new materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance. These materials could be used in various applications, including automotive, aerospace, electronics, and packaging industries.

Upstream product

• 926276-09-7 (1SR,3aRS,6aSR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 1451052-99-5 C₁₃H₂₁NO₄ 
• 1451053-00-1 (R)-tert-butyl 2-(tert-butoxycarbonylamino)-2-((S)-2-methylenecyclopentyl)acetate 
• 402960-06-9 (1S,3aR,6aS)-di-tert-butyl hexahydrocyclo-penta[c]pyrrol-1,2(1H)-dicarboxylate 
• 926276-08-6 (3aR,6aS)-tert-butyl hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 
• 124-38-9 carbon dioxide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 112626-50-3 (3aR,6aS)-octahydrocyclopenta[c]pyrrole hydrochloride 
• 926276-09-7 (3aR,6aS)-2-Boc-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 1227703-21-0 (3aR,6aS)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole 
• 1227703-50-5 (3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-cyanide 
• 791572-14-0 (3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 926276-11-1 (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 926276-09-7 hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester 

Downstream Products

• 1205676-44-3 (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride 
• 1147103-42-1 (1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride 

Relevant articles and documents

N-methyl-D-aspartate receptor modulators and methods of making and using same

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Preparation method for bicyclic pyrrolidine intermediate of telaprevir

The invention discloses a preparation method for a bicyclic pyrrolidine intermediate of telaprevir. The intermediate is (1S,3alphaR,6alphaS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid-ethyl ester hydrochloride. The preparation method comprises the following steps: (1) with 3-azabicyclo[3.3.0]octane hydrochloride as a raw material, carrying out Boc2O protection under the action of inorganic base so as to obtain an intermediate 1; (2) dissolving the intermediate 1 in an organic solvent, adding chiral organic ligand, carrying out a reaction with lithium alkyl at -70 DEG C for 2 h under the protection of nitrogen and introducing dry carbon dioxide so as to obtain an intermediate 2; and (3) adding the intermediate 2 into a saturated hydrogen chloride ethanol solution and carrying out a heating reflux reaction for 3 h so as to obtain the target compound. The preparation method provided by the invention has the advantages of short synthesis route, low cost, high product yield and optical purity and easiness in realization of large-scale production.

Stereoselective lithiation and carboxylation of Boc-protected bicyclopyrrolidine: Synthesis of a key building block for HCV protease inhibitor telaprevir

A stereoselective process for the manufacture of bicyclopyrrolidine 7 to 2 has been developed. The process utilizes a stereoselective lithiation/carboxylation sequence. The achiral diamine ligand DPBP induces excellent diastereocontrol, and resolution with (S)-THNA provides the corresponding salt of 8 in high er and dr. Subsequent processing of 8 gives 2 as the oxalate salt in an overall yield of 27% from 7 (based on total molar charge of 7). Compound 2 was obtained with high chemical and chiral purities. The process was successfully demonstrated on >100 kg scale.