[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

Base Information

Chemical Name:[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester
CAS No.:886447-39-8
Molecular Formula:C₁₉H₂₇N₃O₄
Molecular Weight:361.441
Hs Code.:

Synonyms:[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

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Chemical Property of [4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

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Technology Process of [4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

There total 5 articles about [4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic 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: 56.0%

: 886447-83-2
ethyl [4-[1-tert-butoxycarbonyl-(4S)-phenoxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

: 886447-39-8
[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 886447-39-8
[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 12 h / 20 °C

2: 58 percent / aq. NaOH / tetrahydrofuran / 12 h / 20 °C

3: 69 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 56 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: 93967-75-0
methyl (1-tert-butoxycarbonyl)-(4S)-phenoxy-(2S)-pyrrolidinylcarboxylate

: 886447-39-8
[4-((2S,4S)-4-Phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / aq. NaOH / tetrahydrofuran / 12 h / 20 °C

2: 69 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3: 56 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.bmc.2005.11.058