(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

Base Information

Chemical Name:(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide
CAS No.:1541176-88-8
Molecular Formula:C₂₃H₂₄N₂O₃S
Molecular Weight:408.521
Hs Code.:

Synonyms:(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

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Chemical Property of (-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

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Technology Process of (-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

There total 6 articles about (-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide 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: 67.0%

: 1541176-87-7
(+)-N-{(3R,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-acetamide

: 536-74-3
phenylacetylene

: 1541176-88-8
(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 50 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo4025072

Reference yield:

: 1353342-73-0
(+)-(S)-N-(buta-2,3-dienyl)-N-{2-(tert-butylsulfinylimino)ethyl}-4-methylbenzenesulfonamide

: 1541176-88-8
(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: bis(η3-allyl-μ-chloropalladium(II)) / dichloromethane / 1 h / -40 °C

2: tin(IV) chloride / dichloromethane / 2 h / -78 °C

3: bromine / dichloromethane / 2 h / -78 °C

4: triethylamine / dichloromethane / 1 h / 0 - 20 °C

5: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); bromine; tin(IV) chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo4025072

Reference yield:

: 420132-18-9
N-(buta-2,3-dien-1-yl)-4-methyl-N-(2-oxoethyl)benzenesulfonamide

: 1541176-88-8
(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: diethylene glycol dimethyl ether; titanium(IV) tetraethanolate / tetrahydrofuran / Inert atmosphere; Reflux

2: bis(η3-allyl-μ-chloropalladium(II)) / dichloromethane / 1 h / -40 °C

3: tin(IV) chloride / dichloromethane / 2 h / -78 °C

4: bromine / dichloromethane / 2 h / -78 °C

5: triethylamine / dichloromethane / 1 h / 0 - 20 °C

6: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; titanium(IV) tetraethanolate; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); diethylene glycol dimethyl ether; bromine; tin(IV) chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo4025072