714194-68-0

Usage

Uses

Used in Organic Synthesis:
Octahydro-cyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester serves as a valuable building block in the preparation of an array of pharmaceuticals and agrochemicals. Its structural attributes make it a key component in the development of new molecules with therapeutic and pesticidal properties.
Used in Pharmaceutical Industry:
Within the pharmaceutical sector, Octahydro-cyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester is utilized as a precursor for the synthesis of drugs with potential anti-inflammatory and analgesic effects. Its capacity to modulate biological responses positions it as a candidate for the treatment of various inflammatory conditions and pain management.
Used in Agrochemical Industry:
Similarly, in agrochemical applications, Octahydro-cyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester is employed in the creation of compounds designed to protect crops from pests and diseases, leveraging its reactivity and structural features to enhance agricultural productivity.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 402960-06-9 (1S,3aR,6aS)-di-tert-butyl hexahydrocyclo-penta[c]pyrrol-1,2(1H)-dicarboxylate 
• 1292320-79-6 (1R,2R)-2-(nitromethyl)cyclopentane-1-carbaldehyde 
• 540-88-5 acetic acid tert-butyl ester 
• 1205676-44-3 (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride 
• 1205676-37-4 (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carbonitrile 
• 629-11-8 1,6-hexanediol 
• 1414976-22-9 C₉H₁₅NO₄ 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 
• 1414976-37-6 C₁₉H₂₇NO₂ 
• 926276-11-1 (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid 
• 115-11-7 isobutene 
• 1414976-36-5 C₁₅H₁₉NO₂ 
• 1414976-35-4 C₁₅H₁₈N₂ 

Downstream Products

• 926276-15-5 (1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 907606-68-2 tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt 
• 926276-19-9 (1S,3aR,6aS)-tert-butyl 2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING ESTER COMPOUND

Compound (1) or a salt that is useful as an intermediate for the production of a medicine, an agrochemical or the like can be produced by a process including the following steps: (A) reacting an aldehyde (2) with nitromethane to produce a nitroaldehyde; (B) reacting the nitroaldehyde with an alcohol to produce a nitroacetal; (C) reducing the nitroacetal to produce an aminoacetal; (D) protecting an amino group in the aminoacetal to produce a protected aminoacetal; (E) treating the protected aminoacetal with an acid and subsequently with a base and then reacting the resultant product with a cyanating agent to produce a nitrile; (F) hydrolyzing the nitrile to produce a protected amino acid; and (G) substituting a group R5 in the protected amino acid by a hydrogen atom and protecting a carboxyl group therein.

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.

PROCESS FOR THE PREPARATION OF PROTEASE INHIBITORS

A process for preparing enantioselectively a compound of formula (la) or (Ib) over a compound of formulas I-2—1h.

PROCESSES AND INTERMEDIATES

A process for preparing enantioselectively a compound of formula la or lb: over a compound of formulas 1-2 - Ih:

Processes and intermediates

The invention relates to compounds and processes useful for the preparation of protease inhibitors, particularly serine protease inhibitors. The protease inhibitors are useful for treatment of HCV infections.