(1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate

Base Information

• Chemical Name: (1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate
• CAS No.: 245115-20-2
• Molecular Formula: C13H23NO4
• Molecular Weight: 257
• DSSTox Substance ID: DTXSID90567339
• Wikidata: Q82453199
• Mol file: 245115-20-2.mol

Synonyms:245115-20-2;(1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate;trans-(1R,2R)-2-tert-Butoxycarbonylaminocyclopentanecarboxylic acid ethyl ester;ethyl (1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate;1375312-86-9;(1R,2R)-ethyl 2-(tert-butoxycarbonylamino)cyclopentanecarboxylate;MFCD19689414;Ethyl (1R,2R)-2-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylate;Ethyl (1R,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentane-1-carboxylate;Cyclopentanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl ester, (1R,2R)-;DTXSID90567339;AKOS016014945;ETHYL (1R,2R)-2-((TERT-BUTOXYCARBONYL)AMINO)CYCLOPENTANECARBOXYLATE;FD10580;AS-40248;CS-0313662;(1r,2r)-ethyl 2-(Boc-amino)cyclopentanecarboxylate;J-520462;trans-Ethyl2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate;Ethyl (1R,2R)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylate;trans-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate;ethyl (1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylate

Chemical Property of (1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate

Chemical Property:

• PSA: 68.12000
• LogP: 2.44730
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 257.16270821
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

98% ^*data from raw suppliers

(1R,2R)-Ethyl2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCC1NC(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@@H]1CCC[C@H]1NC(=O)OC(C)(C)C

Technology Process of (1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate

There total 3 articles about (1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate 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: 18.0%

di-tert-butyl dicarbonate (24424-99-5) + trans-ethyl 2-aminocyclopentanecarboxylate (1609100-30-2,752181-59-2) → ethyl (R,R)-tert-butoxycarbonyl-2-aminocyclopentanecarboxylate (245115-20-2)

Guidance literature:

In tetrahydrofuran; for 48h;

DOI:10.1021/ja991185g

Reference yield:

ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate (61586-79-6) → ethyl (R,R)-tert-butoxycarbonyl-2-aminocyclopentanecarboxylate (245115-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HN₃; Ph₃P; diethyl azodicarboxylate / benzene; ethanol / 8 h / 10 - 20 °C

2: Ph₃P; H₂O / tetrahydrofuran / 18 h

3: 18 percent / tetrahydrofuran / 48 h

With tris-(2-chloro-ethyl)-amine; water; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; benzene; 1: Substitution / 2: Reduction / 3: Acylation;

DOI:10.1021/ja991185g

Reference yield:

ethyl (1R,2R)-azidocyclopentanecarboxylate → ethyl (R,R)-tert-butoxycarbonyl-2-aminocyclopentanecarboxylate (245115-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Ph₃P; H₂O / tetrahydrofuran / 18 h

2: 18 percent / tetrahydrofuran / 48 h

With water; triphenylphosphine; In tetrahydrofuran; 1: Reduction / 2: Acylation;

DOI:10.1021/ja991185g

upstream raw materials:

di-tert-butyl dicarbonate

trans-ethyl 2-aminocyclopentanecarboxylate

ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate

Downstream raw materials:

(1R,2R)-2-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid

Refernces