(1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester

Base Information

• Chemical Name: (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester
• CAS No.: 204255-02-7
• Molecular Formula: C14H23NO3
• Molecular Weight: 253.342
• DSSTox Substance ID: DTXSID70942605
• Nikkaji Number: J2.811.734E
• Wikidata: Q82919610
• Mol file: 204255-02-7.mol

Synonyms:204255-02-7;(1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester;ETHYL (1R,5R,6R)-5-(PENTAN-3-YLOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE;ethyl (1R,5R,6R)-5-pentan-3-yloxy-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate;7-Azabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 5-(1-ethylpropoxy)-, ethyl ester, (1R,5R,6R)-;SCHEMBL15481369;DTXSID70942605;HPKPKUHYXGQYRO-JHJVBQTASA-N;AKOS030241737;CS-0164940;(1r,5r,6r)-1-(1-ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-;Ethyl 5-[(pentan-3-yl)oxy]-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate;(1beta,6beta)-5beta-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hepta-3-ene-3-carboxylic acid ethyl ester;Ethyl (1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate (Oseltamivir Impurity pound(c)

Chemical Property of (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester

Chemical Property:

• Melting Point: 110.0 °C
• Boiling Point: 335.5±42.0 °C(Predicted)
• PKA: 5.80±0.60(Predicted)
• PSA: 57.47000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 2.12260
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 253.16779360
• Heavy Atom Count: 18
• Complexity: 336

Purity/Quality:

99% ^*data from raw suppliers

(1R,5R,6R)-1-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC2C1N2)C(=O)OCC
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]2[C@H]1N2)C(=O)OCC
• Uses: Intermediate in the production of Oseltamivir.

Technology Process of (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester

There total 9 articles about (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl 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: 97.0%

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (204254-98-8) → ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate (204255-02-7)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; acetonitrile; at 20 ℃; for 2.16667h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.01.026

Reference yield:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2) → ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate (204255-02-7)

Guidance literature:

With sodium azide; ammonium chloride; trimethylphosphane; Yield given. Multistep reaction; 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h;

DOI:10.1021/jo980330q

Reference yield:

(3R,4S,5S)-4-Amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester → ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate (204255-02-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; at 20 ℃; for 17h;

DOI:10.1021/ol9024716

upstream raw materials:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Downstream raw materials:

ethyl-(3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

C₁₈H₂₈N₄O₄

C₂₁H₃₇N₂O₄P

C₂₁H₃₆N₂O₄

Refernces

• 1、 -. "METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR". Paragraph 0098; 0099. . Retrieved 2014/03/24.
• 2、 Osato, Hiroshi,Jones, Ian L.,Chen, Anqi,Chai, Christina L. L.. "Efficient formal synthesis of oseltamivir phosphate (Tamiflu) with inexpensive D-ribose as the starting material". supporting information; experimental part. p. 60 - 63. Retrieved 2010/03/03.