5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

Base Information

Chemical Name:5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one
CAS No.:141613-02-7
Molecular Formula:C₂₄H₂₈N₂O₄
Molecular Weight:408.497
Hs Code.:

Synonyms:5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

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Chemical Property of 5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

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Technology Process of 5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

There total 9 articles about 5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one 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: 50.0%

: 141613-18-5,141634-74-4
5-(benzyloxy)-1-(tert-butoxycarbonyl)-2-hydroxy-3-methyl-3-<2-oxo-2-(methylamino)ethyl>indole

: 141613-02-7
5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In diethyl ether; at 0 - 20 ℃; for 4.25h;
DOI:10.1021/ja00040a013

Reference yield:

: 21987-24-6
5-(benzyloxy)-3-methyl-1H-indole

: 141613-02-7
5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -75 deg C, 1 h

3: 90 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

4: 58 percent / Zn, CuCl / tetrahydrofuran / 0.08 h / 0 °C

5: 84 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

6: 100 percent / -30 - 20 °C

7: 50 percent / CBr₄, PPh₃ / diethyl ether / 4.25 h / 0 - 20 °C

With dmap; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sec.-butyllithium; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00040a013

Reference yield:

: 1215-59-4
5-benzyloxy-1H-indole

: 141613-02-7
5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<2,3-b>indol-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) EtMgBr / 1.) THF, RT, 4 h, 2.) THF, RT, 18 h

2: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

3: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -75 deg C, 1 h

4: 90 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

5: 58 percent / Zn, CuCl / tetrahydrofuran / 0.08 h / 0 °C

6: 84 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

7: 100 percent / -30 - 20 °C

8: 50 percent / CBr₄, PPh₃ / diethyl ether / 4.25 h / 0 - 20 °C

With dmap; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; ethylmagnesium bromide; sec.-butyllithium; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00040a013