Carbamic acid, [(1R)-4-oxo-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, [(1R)-4-oxo-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester (9CI)
• CAS No.: 657397-01-8
• Molecular Formula: C10H15NO3
• Molecular Weight: 197.234
• Mol file: 657397-01-8.mol

Synonyms:(4R)-4-(tert-butoxycarbonylamino)cyclopenta-2-en-1-one;(R)-CTC-132;(2R)-(4-oxycyclopent-2-enyl)-carbamic acid tert-butyl ester;

Chemical Property of Carbamic acid, [(1R)-4-oxo-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester (9CI)

Chemical Property:

• Boiling Point: 330.1±42.0 °C(Predicted)
• PKA: 11.13±0.20(Predicted)
• PSA: 55.40000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 1.79960

Purity/Quality:

≥98% ^*data from raw suppliers

(R)-tert-Butyl(4-oxocyclopent-2-en-1-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [(1R)-4-oxo-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester (9CI)

There total 19 articles about Carbamic acid, [(1R)-4-oxo-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester (9CI) 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: 97.0%

(R)-(-)-N-(tert-butoxycarbonyl)-6-amino-4-oxo-octa-2,7-diene (667457-57-0) → (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester (657397-01-8)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 16h; Heating;

DOI:10.1021/ol049795v

Reference yield: 80.0%

(+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene (189625-12-5,154802-92-3,178152-48-2) → (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester (657397-01-8)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2004.01.046

Reference yield: 60.0%

(1R)-1-(tert-butoxycarbonylamino)cyclopenta-2-ene (153833-65-9,156731-34-9) → (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester (657397-01-8)

Guidance literature:

With tert.-butylhydroperoxide; palladium 10% on activated carbon; potassium carbonate; In decane; dichloromethane; at 40 ℃; for 48h; stereoselective reaction;

DOI:10.1021/jo402712r

upstream raw materials:

(R)-(-)-N-(tert-butoxycarbonyl)-6-amino-4-oxo-octa-2,7-diene

(R)-(-)-N-(tert-butoxycarbonyl)-6-amino-4-oxo-nona-2,7-diene

(+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene

iminodicarboxylic acid di-tert-butyl ester

Downstream raw materials:

(+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene

(1R,4R)-trans-1-hydroxy-4-<<(tert-butyloxy)carbonyl>amino>-2-cyclopentene

Refernces

• 1、 Davis, Franklin A.,Wu, Yongzhong. "Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using δ-amino β-ketophosphonates and ring-closing metathesis (RCM)". . p. 1269 - 1272. Retrieved 2007/10/03.
• 2、 -. "IMPROVEMENTS IN PHARMACEUTICALLY USEFUL COMPOUNDS". Page 43-44. . Retrieved 2010/11/30.