1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

Base Information

Chemical Name:1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid
CAS No.:1332699-80-5
Molecular Formula:C₂₅H₂₆N₂O₅S
Molecular Weight:466.558
Hs Code.:

Synonyms:1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

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Chemical Property of 1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

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Technology Process of 1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

There total 13 articles about 1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid 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: 93.0%

: 1332699-79-2
1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid methyl ester

: 1332699-80-5
1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

Guidance literature:: With water; potassium carbonate; In methanol; for 48h; Reflux; Inert atmosphere;
DOI:10.1021/ol201980r

Reference yield:

: 1332699-70-3
3-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methoxy-1-(toluene-4-sulfonyl)-2-vinyl-1H-indole

: 1332699-80-5
1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 80 °C / Inert atmosphere

3: sodium tris(acetoxy)borohydride / dichloromethane / 20 °C / Inert atmosphere

4: pyridine / para-xylene / 3 h / 140 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

5: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetonitrile / 3 h / 80 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

6: Grubbs catalyst first generation / dichloromethane / 21 h / 20 - 50 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

7: Grubbs catalyst first generation / dichloromethane / 141 h / 20 - 50 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

8: palladium on carbon; hydrogen / ethyl acetate / 48 h / 20 °C / 760.05 Torr / Inert atmosphere

9: water; potassium carbonate / methanol / 48 h / Reflux; Inert atmosphere

With pyridine; Grubbs catalyst first generation; palladium on carbon; tetrabutyl ammonium fluoride; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; para-xylene; ethyl acetate; acetonitrile;
DOI:10.1021/ol201980r

Reference yield:

: 1332699-71-4
2-[5-methoxy-1-(toluene-4-sulfonyl)-2-vinyl-1H-indol-3-yl]ethanol

: 1332699-80-5
1-{2-[5-methoxy-1-(toluene-4-sulfonyl)-2,3,7,8-hexahydro-(1H-azocino[5,4b]-indol-3-yl)-2,5-dihydro-1H-pyrrole]}-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 80 °C / Inert atmosphere

2: sodium tris(acetoxy)borohydride / dichloromethane / 20 °C / Inert atmosphere

3: pyridine / para-xylene / 3 h / 140 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

4: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetonitrile / 3 h / 80 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

5: Grubbs catalyst first generation / dichloromethane / 21 h / 20 - 50 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

6: Grubbs catalyst first generation / dichloromethane / 141 h / 20 - 50 °C / 12929 Torr / Microwave irradiation; Inert atmosphere

7: palladium on carbon; hydrogen / ethyl acetate / 48 h / 20 °C / 760.05 Torr / Inert atmosphere

8: water; potassium carbonate / methanol / 48 h / Reflux; Inert atmosphere

With pyridine; Grubbs catalyst first generation; palladium on carbon; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; para-xylene; ethyl acetate; acetonitrile;
DOI:10.1021/ol201980r