Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate

Base Information

• Chemical Name: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate
• CAS No.: 207729-00-8
• Molecular Formula: C13H21NO4
• Molecular Weight: 255.314
• Hs Code.: 2924299090
• Mol file: 207729-00-8.mol

Synonyms:1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID ETHYL ESTER;N-Boc ethyl 1-aminocyclopent-3-ene-1-carboxylate;

Chemical Property of Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate

Chemical Property:

• PSA: 68.12000
• LogP: 2.36740
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Ethyl1-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate

There total 10 articles about Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + ethyl 1-aminocyclopent-3-ene-1-carboxylate (199532-88-2) → ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate (207729-00-8)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c01302

Reference yield:

ethyl 1-((4-bromobenzylidene)amino)cyclopent-3-ene-1-carboxylate (199532-83-7) → ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate (207729-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride; water / Inert atmosphere

1.2: Inert atmosphere

2.1: sodium hydrogencarbonate / water / Inert atmosphere

With hydrogenchloride; water; sodium hydrogencarbonate; In water; 1.2: Fischer esterification;

DOI:10.1021/ol201236j

Reference yield:

(2R,5S)-5-allyl-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine (952193-54-3) → ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate (207729-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / 16 h / -78 - 20 °C

2.1: 63 percent / Grubbs second generation catalyst / CH₂Cl₂ / 0.25 h / 140 °C / microwave irradiation

3.1: TFA; water / acetonitrile / 0.33 h / 60 °C / microwave irradiation

4.1: 0.56 g / tetrahydrofuran / 20 h / Heating

With n-butyllithium; water; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2007.06.108

upstream raw materials:

2-tert-butyl-1,3-diisopropylisourea

di-tert-butyl dicarbonate

ethyl 1-aminocyclopent-3-ene-1-carboxylate

tert-butyl alcohol

Downstream raw materials:

C₁₄H₁₅NO₄S

C₁₄H₁₅NO₅S

C₁₇H₂₃NO₅SSi

1-tosyl-3-oxa-1-azaspiro[4.4]non-8-ene-2,7-dione

Refernces

• 1、 -. "RADIONUCLIDE TRACERS OF 1-AMINO-3,4-DIFLUOROCYCLOPENTANE-1-CARBOXYLIC ACID, DERIVATIVES, AND USES THEREOF". Page/Page column 28. . Retrieved 2021/09/26.
• 2、 Kim, Simon,Ciufolini, Marco A.. "Complete facial selectivity in the Diels-Alder reaction of a 5-amino-5-carboxycyclopentadiene derivative". supporting information; scheme or table. p. 3274 - 3277. Retrieved 2011/08/05.