tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Base Information

Chemical Name:tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate
CAS No.:1611480-89-7
Molecular Formula:C₁₈H₂₈N₂O₄
Molecular Weight:336.431
Hs Code.:

Synonyms:tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

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Chemical Property of tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

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Technology Process of tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

There total 6 articles about tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate 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: 62.0%

: 24424-99-5
di-tert-butyl dicarbonate

: ((2S,4S)-4-amino-1-(4-methoxybenzyl)pyrrolidin-2-yl)methanol

: 1611480-89-7
tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: In 1,4-dioxane; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1002/chem.201302423

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 1611480-89-7
tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 8 h / Inert atmosphere; Reflux

2: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 8 h / 65 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

5: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; sodium azide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201302423

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 1611480-89-7
tert-butyl (3S,5S)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1: thionyl chloride / 24 h / 0 °C / Inert atmosphere; Reflux

2: triethylamine / dichloromethane / 8 h / Inert atmosphere; Reflux

3: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 8 h / 65 °C / Inert atmosphere

5: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

6: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; thionyl chloride; sodium azide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201302423