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 5-ethylene ketal

Base Information

• Chemical Name: 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 5-ethylene ketal
• CAS No.: 143076-18-0
• Molecular Formula: C₂₃H₃₀N₂O₇S
• Molecular Weight: 478.566

Synonyms: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 5-ethylene ketal

Chemical Property of 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 5-ethylene ketal

Chemical Property:

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Technology Process of 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 5-ethylene ketal

There total 6 articles about 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 5-ethylene ketal 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: 79.0%

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) + ethylene glycol (107-21-1) → 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 5-ethylene ketal (143076-18-0)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 13h; Heating;

DOI:10.1021/jo00047a031

Reference yield:

N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone (143076-20-4) → 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 5-ethylene ketal (143076-18-0)

Guidance literature:

Multi-step reaction with 5 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

5: 79 percent / TsOH*H₂O / benzene / 13 h / Heating

With 18-crown-6 ether; camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; benzene;

DOI:10.1021/jo00047a031

Reference yield:

3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone (130291-51-9) → 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 5-ethylene ketal (143076-18-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 79 percent / TsOH*H₂O / benzene / 13 h / Heating

With camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; trifluoroacetic acid; In benzene;

DOI:10.1021/jo00047a031

upstream raw materials:

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

ethylene glycol

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

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

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