4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

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Chemical Name:4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid
CAS No.:1192603-42-1
Molecular Formula:C₁₉H₁₇ClN₂O₃
Molecular Weight:356.809
Hs Code.:

Synonyms:4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

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Chemical Property of 4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

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Technology Process of 4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

There total 4 articles about 4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic 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: 45.0%

: 1192603-41-0
ethyl 4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoate

: 1192603-42-1
4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

Guidance literature:: With lithium hydroxide monohydrate; In tetrahydrofuran; ethanol; water; at 20 - 50 ℃; for 3.5h;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 151004-19-2
(4S,5S)-5-methyl-4-hydroxy-2-oxopyrrolidine

: 1192603-42-1
4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

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: 16.5 h / -78 - 20 °C / Inert atmosphere

4.1: 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 4 h / 70 °C

5.1: lithium hydroxide monohydrate / tetrahydrofuran; ethanol; water / 3.5 h / 20 - 50 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; lithium hydroxide monohydrate; sodium bis(2-methoxyethoxy)aluminum dihydride; palladium diacetate; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2012.11.001

Reference yield:

: 1192608-22-2
2-chloro-4-[(2S)-2-methyl-3-oxopyrrolidin-1-yl]benzonitrile

: 1192603-42-1
4-[(2S,3R)-1-(3-chloro-4-cyanophenyl)-3-hydroxy-2-methylpyrrolidin-3-yl]benzoic acid

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 16.5 h / -78 - 20 °C / Inert atmosphere

2.1: 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 4 h / 70 °C

3.1: lithium hydroxide monohydrate / tetrahydrofuran; ethanol; water / 3.5 h / 20 - 50 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; lithium hydroxide monohydrate; palladium diacetate; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2012.11.001