(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

Base Information

Chemical Name:(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole
CAS No.:153914-88-6
Molecular Formula:C₂₉H₂₈N₂O₆S
Molecular Weight:532.617
Hs Code.:

Synonyms:(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

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Chemical Property of (1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

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Technology Process of (1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

There total 10 articles about (1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole 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: 30.0%

: 153914-87-5
(3RS)-3-(Acetoxymethyl)-5-(acetylallylamino)-1-(benzenesulfonyl)-6-(benzyloxy)-4-iodo-2,3-dihydro-1H-indole

: (1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

: 153914-88-6
(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

Guidance literature:: With triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 65 ℃; for 70h;
DOI:10.1021/jo00080a031

Reference yield:

: 119879-90-2
5-(Benzyloxy)-2-bromophenylamine

: 153914-88-6
(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / tetrahydrofuran / 48 h / 66 °C

2: NaH / dimethylformamide; tetrahydrofuran / 1.) 23 deg C, 30 min, 2.) 90 deg C, 2 h

3: 1.) zirconocene (methyl) chloride, t-BuLi, 2.) I₂ / 1.) THF, hexane, -78 deg C, 15 min; 23 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 4 h

4: 95 percent / 90percent HNO₃ / nitromethane / 1.) 0 deg C, 1 h, 2.) r.t., 2 h

6: 87 percent / hydrazine hydrate, FeCl₃*6H₂O, C / methanol / 10 h / Heating

7: 95 percent / CH₃COONa, pyridine / 1.5 h / 60 °C

8: 94 percent / NaH / tetrahydrofuran / 1.) r.t., 15 min, 2.) r.t., 1 h

9: 64 percent / NaOAc, NBu₄Cl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C

With pyridine; zirconocene methyl chloride; tetrabutyl-ammonium chloride; iodine; tert.-butyl lithium; nitric acid; sodium acetate; iron(III) chloride; sodium hydride; hydrazine hydrate; palladium diacetate; In tetrahydrofuran; methanol; nitromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a031

Reference yield:

: 119879-91-3
N-(phenylsulfonyl)-5-(benzyloxy)-2-bromoaniline

: 153914-88-6
(1RS)-6-Acetyl-3-(benzenesulfonyl)-5-(benzyloxy)-1-(acetoxymethyl)-8-methylene-1,2,7,8-tetrahydro-6H-pyrrolo<3,2-e>indole

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide; tetrahydrofuran / 1.) 23 deg C, 30 min, 2.) 90 deg C, 2 h

2: 1.) zirconocene (methyl) chloride, t-BuLi, 2.) I₂ / 1.) THF, hexane, -78 deg C, 15 min; 23 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 4 h

3: 95 percent / 90percent HNO₃ / nitromethane / 1.) 0 deg C, 1 h, 2.) r.t., 2 h

5: 87 percent / hydrazine hydrate, FeCl₃*6H₂O, C / methanol / 10 h / Heating

6: 95 percent / CH₃COONa, pyridine / 1.5 h / 60 °C

7: 94 percent / NaH / tetrahydrofuran / 1.) r.t., 15 min, 2.) r.t., 1 h

8: 64 percent / NaOAc, NBu₄Cl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C

With pyridine; zirconocene methyl chloride; tetrabutyl-ammonium chloride; iodine; tert.-butyl lithium; nitric acid; sodium acetate; iron(III) chloride; sodium hydride; hydrazine hydrate; palladium diacetate; In tetrahydrofuran; methanol; nitromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a031