rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate

Base Information

• Chemical Name: rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate
• CAS No.: 143167-08-2
• Molecular Formula: C₂₁H₂₆N₂O₆S
• Molecular Weight: 434.513
• Mol file: 143167-08-2.mol

Synonyms:

Chemical Property of rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate

There total 5 articles about rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate 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:

N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone (143076-20-4) → rac-Methyl (2S*,3aS*,6aS*,10aS*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate (143167-08-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) 18-crown-6, KN(TMS)2 / 1) THF, toluene, -25 deg C, 5 min, 2) -25 deg C, 1 h

2: 80 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0 °C

3: 2) camphorsulfonic acid / 1) toluene, 11 kbar, r.t., 90 h, 2) THF, r.t., 1 h

4: 1) trifluoroacetic acid, 2) aq.K₂CO₃ / 1) CH₂Cl₂, r.t., 3 h, 2) 3 h

With 18-crown-6 ether; camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00047a031

Reference yield:

2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5) → rac-Methyl (2S*,3aS*,6aS*,10aS*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate (143167-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0 °C

2: 2) camphorsulfonic acid / 1) toluene, 11 kbar, r.t., 90 h, 2) THF, r.t., 1 h

3: 1) trifluoroacetic acid, 2) aq.K₂CO₃ / 1) CH₂Cl₂, r.t., 3 h, 2) 3 h

With camphor-10-sulfonic acid; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00047a031

Reference yield:

2-(tert-Butoxycarbonyl-methyl-amino)-3-[(4aR,8aR)-1,6-dioxo-2-(toluene-4-sulfonyl)-2,3,4,4a,5,6-hexahydro-1H-isoquinolin-8a-yl]-propionic acid methyl ester (130291-54-2,143076-17-9,143076-25-9) → rac-Methyl (2S*,3aS*,6aS*,10aS*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate (143167-08-2) + rac-Methyl (2R*,3aS*,6aS*,10aS*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate (143167-09-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)94730-0

upstream raw materials:

2-(tert-Butoxycarbonyl-methyl-amino)-3-[(4aR,8aR)-1,6-dioxo-2-(toluene-4-sulfonyl)-2,3,4,4a,5,6-hexahydro-1H-isoquinolin-8a-yl]-propionic acid methyl ester

N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone

3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone

2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester