[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

Base Information

Chemical Name:[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate
CAS No.:757191-77-8
Molecular Formula:C₂₃H₂₄N₂O₇S
Molecular Weight:472.519
Hs Code.:

Synonyms:[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

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Chemical Property of [(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

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Technology Process of [(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

There total 5 articles about [(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate 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: 95.0%

: 122-04-3
4-nitro-benzoyl chloride

: 353248-31-4
(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

: 757191-77-8
[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

Guidance literature:: (+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h;

4-nitro-benzoyl chloride; With dmap; In dichloromethane; at 20 ℃; for 13h;
DOI:10.1021/jo0493572

Reference yield:

: 24211-54-9
(S)-5-hydroxypiperidin-2-one

: 757191-77-8
[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / dimethylformamide / 13 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

3.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4.2: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0493572

Reference yield:

: 87179-81-5
(-)-(5S)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one

: 757191-77-8
[(3S)-6-(1-hydroxycyclobutyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridin-3-yl] 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

2.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

3.2: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo0493572