diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

Base Information

Chemical Name:diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate
CAS No.:321851-65-4
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

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Chemical Property of diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

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Technology Process of diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

There total 6 articles about diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate 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: 86.0%

: 105-53-3
diethyl malonate

: 321851-64-3
(2S)-1-benzyloxycarbonyl-[(1S)-2-bromo-1-methylethyl]pyrrolidine

: 321851-65-4
diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

Guidance literature:: diethyl malonate; With sodium hydride; In 1,2-dimethoxyethane;

(2S)-1-benzyloxycarbonyl-[(1S)-2-bromo-1-methylethyl]pyrrolidine; In 1,2-dimethoxyethane; at 60 ℃; for 20h;
DOI:10.1246/bcsj.73.2423

Reference yield:

: (4R,5S)-3-[(2S)-2-{(2S)-1-[2-acetoxyphenylacetoxy]pyrrolidin-2-yl}propionyl]-4-methyl-5-phenyl-2-oxazolidinone

: 321851-65-4
diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Zn; aq. HCl / methanol / 0.5 h / 60 °C

2.1: 3.40 g / KHCO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C / pH 8

3.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 15 h / 5 °C

4.1: 96 percent / PPh₃; CBr₄ / tetrahydrofuran / 0 - 20 °C

5.1: NaH / 1,2-dimethoxy-ethane

5.2: 86 percent / 1,2-dimethoxy-ethane / 20 h / 60 °C

With hydrogenchloride; sodium tetrahydroborate; carbon tetrabromide; sodium hydride; potassium hydrogencarbonate; triphenylphosphine; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water;
DOI:10.1021/ol9905755

Reference yield:

: 321851-63-2
(4R,5S)-3-{(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propionyl}-4-methyl-5-phenyl-2-oxazolidinone

: 321851-65-4
diethyl (2R)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]propylmalonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 15 h / 5 °C

2.1: 96 percent / PPh₃; CBr₄ / tetrahydrofuran / 0 - 20 °C

3.1: NaH / 1,2-dimethoxy-ethane

3.2: 86 percent / 1,2-dimethoxy-ethane / 20 h / 60 °C

With sodium tetrahydroborate; carbon tetrabromide; sodium hydride; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; water;
DOI:10.1021/ol9905755