ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate

Base Information

• Chemical Name: ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate
• CAS No.: 701305-27-3
• Molecular Formula: C₂₉H₃₂N₂O₅S
• Molecular Weight: 520.649
• Mol file: 701305-27-3.mol

Synonyms:ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate

Chemical Property of ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate

There total 4 articles about ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate 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:

ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)-propenoate → ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate (701305-27-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20 ℃; under 760 Torr;

DOI:10.1016/j.bmc.2004.02.032

Reference yield:

2-(hydroxymethyl)benzo[b]thiophene-5-carbonitrile (105191-15-9) → ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate (701305-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂; pyridine / diethyl ether / 2 h / 20 °C

2: 6.3 g / xylene / 10 h / Heating

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol; tetrahydrofuran / 1 h / 20 °C

4: 2.2 g / H₂ / Pd/C / ethanol; tetrahydrofuran / 20 °C / 760 Torr

With pyridine; thionyl chloride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; xylene; 3: Wittig reaction;

DOI:10.1016/j.bmc.2004.02.032

Reference yield:

2-chloromethyl-benzo[b]thiophene-5-carbonitrile (544694-71-5) → ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1-benzothien-2-yl)propanoate (701305-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 6.3 g / xylene / 10 h / Heating

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol; tetrahydrofuran / 1 h / 20 °C

3: 2.2 g / H₂ / Pd/C / ethanol; tetrahydrofuran / 20 °C / 760 Torr

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; ethanol; xylene; 2: Wittig reaction;

DOI:10.1016/j.bmc.2004.02.032

upstream raw materials:

2-(hydroxymethyl)benzo[b]thiophene-5-carbonitrile

2-chloromethyl-benzo[b]thiophene-5-carbonitrile

Downstream raw materials:

ethyl 3-(5-amidino-1-benzothien-2-yl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoate