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

Base Information

Chemical Name:tert-butyl (3S,5R)-5-(fluoromethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate
CAS No.:1611480-93-3
Molecular Formula:C₁₈H₂₇FN₂O₃
Molecular Weight:338.422
Hs Code.:

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

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

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

There total 8 articles about tert-butyl (3S,5R)-5-(fluoromethyl)-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: 51.0%

: 1318128-67-4
tert-butyl (3S,5R)-5-(hydroxymethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

: 1611480-92-2
tert-butyl ((3S,5S)-5-fluoro-1-(4-methoxybenzyl)piperidin-3-yl)carbamate

: 1611480-93-3
tert-butyl (3S,5R)-5-(fluoromethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: With diethylamino-sulfur trifluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1002/chem.201302423

Reference yield:

: 1318129-73-5
methyl (2R,4R)-4-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2-carboxylate

: 1611480-92-2
tert-butyl ((3S,5S)-5-fluoro-1-(4-methoxybenzyl)piperidin-3-yl)carbamate

: 1611480-93-3
tert-butyl (3S,5R)-5-(fluoromethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 14 h / 0 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 22 h / 20 - 65 °C / Inert atmosphere

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

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

5: diethylamino-sulfur trifluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

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

Reference yield:

: C₁₅H₂₁NO₆S

: 1611480-92-2
tert-butyl ((3S,5S)-5-fluoro-1-(4-methoxybenzyl)piperidin-3-yl)carbamate

: 1611480-93-3
tert-butyl (3S,5R)-5-(fluoromethyl)-1-(4-methoxybenzyl)pyrrolidin-3-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium azide / N,N-dimethyl-formamide / 22 h / 20 - 65 °C / Inert atmosphere

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

3: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

4: diethylamino-sulfur trifluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

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