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

Base Information

• Chemical Name: 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid
• CAS No.: 1192609-56-5
• Molecular Formula: C₁₉H₁₉N₃O₄
• Molecular Weight: 353.378

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

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

Chemical Property:

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

There total 6 articles about 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid 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: 95.0%

ethyl 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylate (1192609-54-3) → 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid (1192609-56-5)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2012.11.001

Reference yield:

(4S,5S)-5-methyl-4-hydroxy-2-oxopyrrolidine (151004-19-2) → 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid (1192609-56-5)

Guidance literature:

Multi-step reaction with 5 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

5.1: sodium hydroxide; water / tetrahydrofuran; ethanol / 2 h / 20 °C

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

DOI:10.1016/j.bmc.2012.11.001

Reference yield:

4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile (1192608-98-2) → 5-[(2S,3R)-1-(4-cyano-3-methoxyphenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]pyridine-2-carboxylic acid (1192609-56-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: sodium hydroxide; water / tetrahydrofuran; ethanol / 2 h / 20 °C

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

DOI:10.1016/j.bmc.2012.11.001

upstream raw materials:

(4S,5S)-5-methyl-4-hydroxy-2-oxopyrrolidine

2-methoxy-4-fluorobenzonitrile

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

2-methoxy-4-[(2S)-2-methyl-3-oxopyrrolidin-1-yl]benzonitrile

Downstream raw materials:

C₂₀H₂₂N₄O₃

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