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

Base Information

Chemical Name:ethyl [4-[1-tert-butoxycarbonyl-(4S)-phenoxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate
CAS No.:886447-83-2
Molecular Formula:C₂₄H₃₅N₃O₆
Molecular Weight:461.558
Hs Code.:

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

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Chemical Property of ethyl [4-[1-tert-butoxycarbonyl-(4S)-phenoxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

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Technology Process of ethyl [4-[1-tert-butoxycarbonyl-(4S)-phenoxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

There total 4 articles about ethyl [4-[1-tert-butoxycarbonyl-(4S)-phenoxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 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: 69.0%

: 40004-08-8
1-(Ethoxycarbonylmethyl)piperazine

: 147266-79-3,158459-12-2,2380783-50-4,147267-15-0
(2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid

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

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 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

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

Guidance literature:: Multi-step reaction with 3 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

With sodium hydroxide; di-isopropyl azodicarboxylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 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

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

Guidance literature:: Multi-step reaction with 2 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

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