ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Base Information

• Chemical Name: ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate
• CAS No.: 1192609-54-3
• Molecular Formula: C₂₁H₂₃N₃O₄
• Molecular Weight: 381.431
• Mol file: 1192609-54-3.mol

Synonyms:ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Chemical Property of ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate

There total 4 articles about ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate 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: 66.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + 4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile (1192603-74-9) → ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate (1192609-54-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 70 ℃; for 16h;

DOI:10.1016/j.bmc.2012.11.001

Reference yield:

4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile (1192608-98-2) → ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate (1192609-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 1 h / 20 °C

2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 16 h / 70 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; palladium diacetate; sulfur trioxide pyridine complex; triethylamine; In diethyl ether; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.11.001

Reference yield:

2-methoxy-4-fluorobenzonitrile (191014-55-8) → ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate (1192609-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium bis(2-methoxyethoxy)aluminum dihydride / toluene; tetrahydrofuran / 3 h / 5 - 70 °C

1.2: 16 h / 20 °C

1.3: 1 h / 100 °C

2.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 1 h / 20 °C

3.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 16 h / 70 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; sodium bis(2-methoxyethoxy)aluminum dihydride; palladium diacetate; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2012.11.001

upstream raw materials:

2-methoxy-4-fluorobenzonitrile

ethanol

carbon monoxide

4-[(2S,3R)-3-(6-bromopyridin-3-yl)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile

Downstream raw materials:

5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid

C₂₀H₂₂N₄O₃