5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

Base Information

Chemical Name:5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester
CAS No.:827575-38-2
Molecular Formula:C₂₃H₂₃NO₄S
Molecular Weight:409.506
Hs Code.:

Synonyms:5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

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Chemical Property of 5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

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Technology Process of 5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

There total 5 articles about 5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester 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%

: 827575-29-1
4-but-3-ynyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine

: 1885-14-9
phenyl chloroformate

: 827575-38-2
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

Guidance literature:: 4-but-3-ynyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.833333h;

phenyl chloroformate; In diethyl ether; hexane; at -78 - 20 ℃;
DOI:10.1021/ol047696b

Reference yield:

: 827575-53-1
6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine

: 827575-38-2
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Mg / tetrahydrofuran / 1.17 h

1.2: 83 percent / CuBr*DMS / tetrahydrofuran / 22 h / -15 - 20 °C

2.1: 96 percent / K₂CO₃ / methanol / 15 h / 20 °C

3.1: n-BuLi / diethyl ether; hexane / 0.83 h / -78 °C

3.2: 51 percent / diethyl ether; hexane / -78 - 20 °C

With n-butyllithium; potassium carbonate; magnesium; In tetrahydrofuran; methanol; diethyl ether; hexane;
DOI:10.1021/ol047696b

Reference yield:

: 827575-52-0
3-bromo-2-methoxy-1-(toluene-4-sulfonyl)piperidine

: 827575-38-2
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / DBU / dimethylformamide / 20 h / 90 °C

2.1: Mg / tetrahydrofuran / 1.17 h

2.2: 83 percent / CuBr*DMS / tetrahydrofuran / 22 h / -15 - 20 °C

3.1: 96 percent / K₂CO₃ / methanol / 15 h / 20 °C

4.1: n-BuLi / diethyl ether; hexane / 0.83 h / -78 °C

4.2: 51 percent / diethyl ether; hexane / -78 - 20 °C

With n-butyllithium; potassium carbonate; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol047696b