402960-06-9

Basic information

• Product Name: Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester
• Synonyms: Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester;Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1,2-bis(1,1-diMethylethyl) ester, (1S,3aR,6aS)-;(3aR,6aS)-di-tert-butyl hexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylate;(1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic Acid Bis(tert-butyl) Ester;(1S,3aR,6aS)-Di-tert-butyl hexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylate;di-tert-butyl (1S,3aR,6aS)-hexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylate
• CAS NO: 402960-06-9
• Molecular Formula: C17H27NO4
• Molecular Weight: 309.40058
• Mol File: 402960-06-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane
• CAS DataBase Reference: Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester(402960-06-9)
• EPA Substance Registry System: Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester(402960-06-9)

Safety Data

• Hazardous Substances Data: 402960-06-9(Hazardous Substances Data)

Usage

Description

Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester is a complex organic compound characterized by its unique molecular structure and oily chemical properties. It is a derivative of cyclopenta[c]pyrrole-1,2-dicarboxylic acid with two tert-butyl ester groups attached, which contribute to its stability and reactivity in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester is used as a key intermediate compound for the synthesis of peptidomimetic protease inhibitors. These inhibitors are essential in the development of drugs targeting various diseases, including viral infections and cancer, due to their ability to mimic the structure of natural peptides and block the action of specific proteases.
Used in Chemical Research:
As an oily liquid with distinct chemical properties, Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester can be utilized in various chemical research applications. It can serve as a starting material or a building block for the synthesis of more complex molecules with potential applications in materials science, pharmaceuticals, and other industries.
Used in Material Science:
The unique structure and properties of Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester make it a candidate for the development of novel materials with specific characteristics. It can be used in the creation of new polymers, coatings, or other advanced materials with tailored properties for various applications, such as improved mechanical strength, thermal stability, or chemical resistance.

Upstream product

• 926276-08-6 (3aR,6aS)-tert-butyl hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 
• 112626-50-3 (3aR,6aS)-octahydrocyclopenta[c]pyrrole hydrochloride 
• 926276-09-7 (1SR,3aRS,6aSR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 1227704-10-0 (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1451053-01-2 (R)-tert-butyl 2-(tert-butoxycarbonylamino)-2-(((1S,2R)-2-hydroxymethyl)cyclopentyl)acetate 
• 1451053-00-1 (R)-tert-butyl 2-(tert-butoxycarbonylamino)-2-((S)-2-methylenecyclopentyl)acetate 
• 1451052-99-5 C₁₃H₂₁NO₄ 

Downstream Products

• 597569-42-1 (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclo-penta[c]pyrrole-1-carboxylic acid 
• 714194-68-0 tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 907606-68-2 tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt 

Relevant articles and documents

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.