(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

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Chemical Name:(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate
CAS No.:1508298-45-0
Molecular Formula:C₁₈H₂₃NO₆S
Molecular Weight:381.45
Hs Code.:

Synonyms:(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

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Technology Process of (2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

There total 7 articles about (2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-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: 77.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 1508298-44-9
(2S,3S,4S)-tert-butyl 3-(2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

: 1508298-45-0
(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: (2S,3S,4S)-tert-butyl 3-(2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate; With Jones reagent; In acetone; at 0 ℃; for 0.166667h;

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

diazomethane; In diethyl ether; at 0 ℃; for 0.25h;
DOI:10.1021/ol4028557

Reference yield:

: 1508298-41-6
(S,E)-tert-butyl 2-(N-(4-bromobut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate

: 1508298-45-0
(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridinium p-toluenesulfonate / water; acetone / 27 h / 60 °C / Inert atmosphere

2.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 - 20 °C / Inert atmosphere

4.1: mercury(II) diacetate / water; tetrahydrofuran / 2.5 h / -10 - 20 °C / Inert atmosphere

5.1: Jones reagent / acetone / 0.17 h / 0 °C

5.2: 1 h / 0 °C / Inert atmosphere

5.3: 0.25 h / 0 °C

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Jones reagent; mercury(II) diacetate; tert.-butyl lithium; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; water; acetone; pentane; 2.1: |Tsuji-Trost Allylation;
DOI:10.1021/ol4028557

Reference yield:

: 1508298-40-5
(S)-tert-butyl 4,4-dimethoxy-2-(4-methylphenylsulfonamido)butanoate

: 1508298-45-0
(2S,3S,4S)-methyl 3-(2-methoxy-2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / dimethyl sulfoxide / 0.25 h / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / water; acetone / 27 h / 60 °C / Inert atmosphere

3.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 - 20 °C / Inert atmosphere

5.1: mercury(II) diacetate / water; tetrahydrofuran / 2.5 h / -10 - 20 °C / Inert atmosphere

6.1: Jones reagent / acetone / 0.17 h / 0 °C

6.2: 1 h / 0 °C / Inert atmosphere

6.3: 0.25 h / 0 °C

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Jones reagent; mercury(II) diacetate; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; In tetrahydrofuran; water; dimethyl sulfoxide; acetone; pentane; 3.1: |Tsuji-Trost Allylation;
DOI:10.1021/ol4028557