(3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor

Base Information

• Chemical Name: (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor
• CAS No.: 907606-68-2
• Molecular Formula: C12H21NO2·C2H2O4
• Molecular Weight: 301.34
• Hs Code.: 2902190000
• Mol file: 907606-68-2.mol

Synonyms:Cyclopenta[c]pyrrole-1-carboxylic acid, octahydro-, 1,1-dimethylethyl ester, (1S,3aR,6aS)-, ethanedioate (1:1);(1S,3aR,6aS)-Octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester oxalate;

Chemical Property of (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• PSA: 112.93000
• Density: 1.26 at 20℃
• LogP: 1.20060
• Storage Temp.: 2-8°C

Purity/Quality:

98.0%Min ^*data from raw suppliers

(1S,3AR,6aS)-tert-Butyl octahydrocyclopenta-[c]pyrrole-1-carboxylate oxalate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor

There total 7 articles about (3aR,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrol-2-iuM carboxyfor 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: 81.0%

(1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt (1227704-10-0) + oxalic acid (144-62-7,97993-78-7) + tert-butyl alcohol (75-65-0) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Guidance literature:

(1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt; With sodium hydrogen sulfate; In tert-butyl methyl ether; water; for 0.5h;

tert-butyl alcohol; With dmap; sodium hydrogen sulfate; di-tert-butyl dicarbonate; In tert-butyl methyl ether; water; at 20 - 25 ℃; for 5 - 6h;

oxalic acid; With methanesulfonic acid; potassium carbonate; more than 3 stages; Product distribution / selectivity;

Reference yield: 59.7%

acetic acid tert-butyl ester (540-88-5) + (1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride (1219204-23-5) + oxalic acid (144-62-7,97993-78-7) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Guidance literature:

acetic acid tert-butyl ester; (1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride; In dichloromethane; at 0 - 21 ℃;

With methanesulfonic acid; In dichloromethane; water; at 0 - 21 ℃; for 18.25h; Sealed tube;

oxalic acid;

Reference yield:

acetic acid tert-butyl ester (540-88-5) + (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride (1205676-44-3,1219204-23-5) + oxalic acid (144-62-7,97993-78-7) → tert-butyl (1S,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylate oxalic acid salt (907606-68-2)

Guidance literature:

acetic acid tert-butyl ester; (1S,3αR,6αS)-octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride; With methanesulfonic acid; In chloroform; at 0 - 25 ℃; for 18h;

oxalic acid; In isopropyl alcohol; at 75 - 80 ℃; for 0.5h;

upstream raw materials:

acetic acid tert-butyl ester

(1R,3aR,6aS)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid hydrochloride

oxalic acid

(1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (S)-1,2,3,4-tetrahydro-1-naphthylammonium salt

Downstream raw materials:

(1S,3aR,6aS)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

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

Refernces

• 1、 Tanoury, Gerald J.,Chen, Minzhang,Dong, Yong,Forslund, Raymond,Jurkauskas, Valdas,Jones, Andrew D.,Belmont, Daniel. "Stereoselective lithiation and carboxylation of Boc-protected bicyclopyrrolidine: Synthesis of a key building block for HCV protease inhibitor telaprevir". . p. 1234 - 1244. Retrieved 2014/12/10.
• 2、 -. "Processes and intermediates". Page/Page column 43-44. . Retrieved 2010/11/26.