toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester
• CAS No.: 916306-98-4
• Molecular Formula: C₃₅H₃₆N₄O₅S
• Molecular Weight: 624.761
• Mol file: 916306-98-4.mol

Synonyms:toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester

Chemical Property of toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester

There total 9 articles about toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl 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:

(6aR,9R)-4-(2-hydroxy-ethyl)-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester (916306-98-4)

Guidance literature:

With dmap; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1016/j.bmcl.2011.06.070

Reference yield:

(6aR,9R)-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide (916306-10-0) → toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester (916306-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃NBnCl; sodium hydroxide / dichloromethane / 1 h / 0 - 5 °C

2: lithium borohydride / tetrahydrofuran / 5 h / 0 - 5 °C

3: dmap / dichloromethane / 2 h / 25 °C

With dmap; lithium borohydride; Et₃NBnCl; sodium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2011.06.070

Reference yield:

(6aR,9R)-7-phenylcarbamoyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (916306-96-2) → toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester (916306-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C

2.1: sodium hydroxide; water / N-benzyl-N,N,N-triethylammonium chloride / dichloromethane / 1 h / 0 - 5 °C

3.1: lithium borohydride / tetrahydrofuran / 4.5 h / 0 - 20 °C

3.2: 0 °C

4.1: dmap / dichloromethane / 3.5 h / 0 - 20 °C

With dmap; sodium hydroxide; lithium borohydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; dichloromethane;

upstream raw materials:

p-toluenesulfonyl chloride

(6aR,9R)-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide

(6aR,9R)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester

(6aR,9R)-7-phenylcarbamoyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid