tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
CAS No.:1037368-59-4
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

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Chemical Property of tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

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Technology Process of tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

There total 2 articles about tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-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%

: 915795-74-3
tert-butyl 3-(hydroxymethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

: 105-36-2
ethyl bromoacetate

: 1037368-59-4
tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 18.5h;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: 915302-93-1
2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-4-carboxylic acid tert-butyl ester

: 1037368-59-4
tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C

2: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 18.5 h / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: 1037368-59-4
tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

: 1037368-60-7
tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

Guidance literature:: tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1.5h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 1h;

With water; ammonium chloride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; more than 3 stages;