8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline

Base Information

• Chemical Name: 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline
• CAS No.: 130291-52-0
• Molecular Formula: C₂₃H₂₈N₂O₈S
• Molecular Weight: 492.55
• Mol file: 130291-52-0.mol

Synonyms:

Chemical Property of 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline

There total 4 articles about 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline 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) → 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline (130291-52-0,143076-23-7,143104-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) KN(TMS)2 / 1) THF, -60 deg C, 2) THF, -30 to -20 deg C, 1 h

2: 88 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: 2) camphorsulfonic acid / 1) p-cymene, reflux, 5 h, 2) THF, r.t.

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

DOI:10.1021/jo00047a031

Reference yield:

2-(Methoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-48-4) → 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline (130291-52-0,143076-23-7,143104-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 2) camphorsulfonic acid / 1) p-cymene, reflux, 5 h, 2) THF, r.t.

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

DOI:10.1021/jo00047a031

Reference yield:

1-(toluene-4-sulfonyl)piperidin-2-one (23438-61-1) → 8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline (130291-52-0,143076-23-7,143104-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -60 °C

2: 1) KN(TMS)2 / 1) THF, -60 deg C, 2) THF, -30 to -20 deg C, 1 h

3: 88 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

4: 2) camphorsulfonic acid / 1) p-cymene, reflux, 5 h, 2) THF, r.t.

With camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00047a031

upstream raw materials:

danishefsky's diene

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

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

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

Downstream raw materials:

(1R,6R)-13-Methyl-2,8,12-trioxo-3-(toluene-4-sulfonyl)-11-oxa-3,13-diaza-tricyclo[8.5.0.0^1,6]pentadecane-14-carboxylic acid methyl ester

Refernces

• 1、 Torisawa, Yasuhiro,Nakagawa, Masako,Arai, Hitoe,Lai, Ziping,Hino, Tohru,et al.. "SYNTHETIC STUDIES ON MANZAMINE A II; A NOVEL DIELS-ALDER APPROACH TO THE PYRROLOISOQUINOLINE SKELETON". . p. 3195 - 3198. Retrieved 2007/10/02.