tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

Base Information

Chemical Name:tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate
CAS No.:1235568-25-8
Molecular Formula:C₂₀H₂₈N₄O₄
Molecular Weight:388.467
Hs Code.:

Synonyms:tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

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Chemical Property of tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

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Technology Process of tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

There total 1 articles about tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-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: 84.0%

: 1235568-24-7
tert-butyl (2S,5S)-1-benzyl-5-(2-ethoxycarbonylmethyl)pyrrolidine-2-carboxylate

: 1235568-25-8
tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

Guidance literature:: tert-butyl (2S,5S)-1-benzyl-5-(2-ethoxycarbonylmethyl)pyrrolidine-2-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.75h; Inert atmosphere;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene; at -78 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo1008433

Reference yield: 94.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1235568-25-8
tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

: 1235568-28-1
tert-butyl (2S,5S)-1-benzyl-5-((S)-1-(tert-butoxycarbonylamino)-2-ethoxycarbonylmethyl)pyrrolidine-2-carboxylate

Guidance literature:: tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate; With triphenylphosphine; In tetrahydrofuran; for 2h; Reflux; Inert atmosphere;

With water; In tetrahydrofuran; for 24h; Inert atmosphere; Reflux;

di-tert-butyl dicarbonate; With triethylamine; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jo1008433

Reference yield:

: 1235568-25-8
tert-butyl (2S,5S)-5-((S)-1-azido-2-ethoxycarbonylmethyl)-1-benzylpyrrolidine-2-carboxylate

: 1235568-28-1
tert-butyl (2S,5S)-1-benzyl-5-((S)-1-(tert-butoxycarbonylamino)-2-ethoxycarbonylmethyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: triphenylphosphine / tetrahydrofuran; water

2: triethylamine

With triethylamine; triphenylphosphine; In tetrahydrofuran; water;
DOI:10.1016/j.bmcl.2011.09.079