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

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Chemical Name:5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid dimethylamide
CAS No.:827575-44-0
Molecular Formula:C₁₉H₂₄N₂O₃S
Molecular Weight:360.477
Hs Code.:

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

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

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

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

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

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: 827575-44-0
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid dimethylamide

Guidance literature:: 4-but-3-ynyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine; With methyllithium; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃; for 1.33333h;

N,N-Dimethylcarbamoyl chloride; In tetrahydrofuran; diethyl ether; at -20 - 20 ℃;
DOI:10.1021/ol047696b

Reference yield:

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

: 827575-44-0
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid dimethylamide

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: MeLi / tetrahydrofuran; diethyl ether / 1.33 h / -78 - -20 °C

3.2: 67 percent / tetrahydrofuran; diethyl ether / -20 - 20 °C

With methyllithium; potassium carbonate; magnesium; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/ol047696b

Reference yield:

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

: 827575-44-0
5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-2-ynoic acid dimethylamide

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: MeLi / tetrahydrofuran; diethyl ether / 1.33 h / -78 - -20 °C

4.2: 67 percent / tetrahydrofuran; diethyl ether / -20 - 20 °C

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