(2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

Base Information

Chemical Name:(2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione
CAS No.:1452925-73-3
Molecular Formula:C₂₂H₂₂BrNO₆S
Molecular Weight:508.39
Hs Code.:

Synonyms:

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Chemical Property of (2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

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Technology Process of (2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

There total 7 articles about (2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione 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:

: 98-59-9
p-toluenesulfonyl chloride

: 1452925-73-3
(2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / dichloromethane / 10 h / 0 - 25 °C

2.1: Trimethylacetic acid / toluene / 20 h / 110 °C

3.1: hydrogenchloride / tetrahydrofuran; diethyl ether; water / 9 h / 25 °C

3.2: 10 h / 50 °C

4.1: N-Bromosuccinimide / acetonitrile / 4 h / 0 - 25 °C

5.1: sodium hydroxide / tetrahydrofuran; methanol / 0.5 h / 25 °C

6.1: 3-chloro-benzenecarboperoxoic acid; 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide) / dichloromethane / 21 h / -20 °C

7.1: dichloromethane / 12 h / -20 - 25 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide); 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; Trimethylacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; 7.1: |Diels-Alder Cycloaddition;
DOI:10.1002/anie.201303559

Reference yield:

: 1452925-64-2
3-(7-bromo-4-hydroxy-1-tosylindolin-5-yl)propanoic acid

: 1452925-73-3
(2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid; 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide) / dichloromethane / 21 h / -20 °C

2: dichloromethane / 12 h / -20 - 25 °C

With 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide); 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 2: |Diels-Alder Cycloaddition;
DOI:10.1002/anie.201303559

Reference yield:

: 1452925-61-9
C₂₂H₂₇NO₅S

: 1452925-73-3
(2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrogenchloride / tetrahydrofuran; diethyl ether; water / 9 h / 25 °C

1.2: 10 h / 50 °C

2.1: N-Bromosuccinimide / acetonitrile / 4 h / 0 - 25 °C

3.1: sodium hydroxide / tetrahydrofuran; methanol / 0.5 h / 25 °C

4.1: 3-chloro-benzenecarboperoxoic acid; 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide) / dichloromethane / 21 h / -20 °C

5.1: dichloromethane / 12 h / -20 - 25 °C

With hydrogenchloride; N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol; N,N'-(2S,2'S)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide); 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; 5.1: |Diels-Alder Cycloaddition;
DOI:10.1002/anie.201303559