HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER

Base Information

• Chemical Name: HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER
• CAS No.: 597569-42-1
• Molecular Formula: C13H21NO4
• Molecular Weight: 255.314
• Mol file: 597569-42-1.mol

Synonyms:HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER

Chemical Property of HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER

Chemical Property:

• Boiling Point: 386.0±25.0 °C(Predicted)
• PKA: 4.05±0.20(Predicted)
• PSA: 66.84000
• Density: 1.196
• LogP: 2.04450
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2(1H)-dicarboxylicAcid2-(tert-Butyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic Acid 2-(tert-Butyl) Ester can be used in the preparation of peptidomimetic protease inhibitors.

Technology Process of HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER

There total 29 articles about HEXAHYDRO-CYCLOPENTA[C]PYRROLE-1,2-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt (1227704-10-0) → (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclo-penta[c]pyrrole-1-carboxylic acid (597569-42-1,926276-09-7)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 0.25h; enantioselective reaction;

Reference yield: 94.0%

(R)-1-phenylethanaminium (1S,3aR,6aS)-2-(t-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylate → (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclo-penta[c]pyrrole-1-carboxylic acid (597569-42-1,926276-09-7)

Guidance literature:

With sodium hydrogen sulfate; In tert-butyl methyl ether; water;

Reference yield: 72.0%

(1S,3aR,6aS)-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester ethyl ester (1053232-60-2) → (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclo-penta[c]pyrrole-1-carboxylic acid (597569-42-1,926276-09-7)

Guidance literature:

(1S,3aR,6aS)-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester ethyl ester; With ethanol; sodium hydroxide; at 20 ℃; for 3h;

With hydrogenchloride; In water;

upstream raw materials:

(1SR,3aRS,6aSR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid

(1S,3aR,6aS)-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester ethyl ester

C₁₃H₂₁NO₄

(R)-tert-butyl 2-(tert-butoxycarbonylamino)-2-((S)-2-methylenecyclopentyl)acetate

Downstream raw materials:

(1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride

(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride

Refernces

• 1、 -. "A process for the preparation of intermediates telaprevir". . . Retrieved 2017/03/14.
• 2、 -. "Process for the preparation of a viral protease inhibitor and its intermediates". Paragraph 0086. . Retrieved 2014/11/27.