methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

Base Information

Chemical Name:methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate
CAS No.:1630067-79-6
Molecular Formula:C₂₄H₂₉NO₄
Molecular Weight:395.499
Hs Code.:

Synonyms:methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

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Chemical Property of methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

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Technology Process of methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

There total 7 articles about methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-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: 91.9%

: 1630067-78-5
methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(2-methoxyphenyl)hex-4-en-1-yl}carbamate

: 1630067-79-6
methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1002/ejoc.201402452

Reference yield:

: 1630067-74-1
(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-(methoxymethoxy)-2-(2-methoxyphenyl)hex-4-enoic acid

: 1630067-79-6
methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: di-tert-butyl dicarbonate; pyridine / ethyl acetate / 3.5 h / 20 °C / Inert atmosphere

1.2: 1 h / Inert atmosphere

2.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 21 h / 0 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: hydrogenchloride / methanol / 8 h / 0 - 20 °C / Inert atmosphere

5.1: dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; aluminum (III) chloride; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; di-tert-butyl dicarbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201402452

Reference yield:

: 1630067-73-0
(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 2-(2-methoxyphenyl)acetate

: 1630067-79-6
methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 2.75 h / -78 - -20 °C / Inert atmosphere

2.1: di-tert-butyl dicarbonate; pyridine / ethyl acetate / 3.5 h / 20 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

3.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 21 h / 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: hydrogenchloride / methanol / 8 h / 0 - 20 °C / Inert atmosphere

6.1: dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; aluminum (III) chloride; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; chloro-trimethyl-silane; di-tert-butyl dicarbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201402452