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

Base Information

• Chemical Name: methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate
• CAS No.: 1630067-80-9
• Molecular Formula: C₂₃H₂₉NO₅
• Molecular Weight: 399.487

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate

There total 8 articles about methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-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: 90.3%

methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate (1630067-79-6) → methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate (1630067-80-9)

Guidance literature:

With sodium tetrahydroborate; ozone; In methanol; dichloromethane; at -78 - 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201402452

Reference yield:

(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 2-(2-methoxyphenyl)acetate (1630067-73-0) → methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate (1630067-80-9)

Guidance literature:

Multi-step reaction with 7 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

7.1: ozone; sodium tetrahydroborate / dichloromethane; methanol / 1 h / -78 - 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; aluminum (III) chloride; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; lithium aluminium tetrahydride; chloro-trimethyl-silane; di-tert-butyl dicarbonate; ozone; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1002/ejoc.201402452

Reference yield:

(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-(methoxymethoxy)-2-(2-methoxyphenyl)hex-4-enoic acid (1630067-74-1) → methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate (1630067-80-9)

Guidance literature:

Multi-step reaction with 6 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

6.1: ozone; sodium tetrahydroborate / dichloromethane; methanol / 1 h / -78 - 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; aluminum (III) chloride; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; lithium aluminium tetrahydride; di-tert-butyl dicarbonate; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1002/ejoc.201402452

upstream raw materials:

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

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

(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-(methoxymethoxy)-2-(2-methoxyphenyl)hex-4-enamide

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

Downstream raw materials:

methyl (2S,3S,4S)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate

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