N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

Base Information

Chemical Name:N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide
CAS No.:470465-24-8
Molecular Formula:C₂₄H₂₈BrNO₄S
Molecular Weight:506.461
Hs Code.:

<i>N</i>-(2-bromo-ethyl)-<i>N</i>-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3<i>H</i>-cyclopenta[<i>a</i>]naphthalen-4-yl)-benzenesulfonamide

Synonyms:N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

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Chemical Property of N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

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Technology Process of N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

There total 13 articles about N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide 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: 83.0%

: 106-93-4
ethylene dibromide

: 470465-23-7
N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

: 470465-24-8
N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

Guidance literature:: With sodium hydroxide; tetrabutylammomium bromide; In water; toluene; at 100 ℃; for 0.666667h;
DOI:10.1021/ja027882h

Reference yield:

: 52644-01-6
5,6-dimethoxy-2-tetralone

: 470465-24-8
N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 39.0 g / sodium methoxide / methanol / 2 h / Heating

2.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 80 percent / tetrahydrofuran; hexane / 1 h / 20 °C

3.1: 43 percent / p-toluenesulfonic acid monohydrate; triethyl orthoformate / CH₂Cl₂ / 19 h / 25 °C

4.1: 77 percent / potassium bis(trimethylsilyl)amide / diethyl ether; toluene / 2 h / 20 °C

5.1: 80 percent / aq. AcOH / 4 h / Heating

6.1: 97 percent / L-selectride / tetrahydrofuran / 17 h / 0 °C

7.1: diphenylphosphoryl azide; diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 17 h / 20 °C

8.1: LiAlH₄ / ethanol; diethyl ether / 2 h / 20 °C

9.1: 528 mg / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

10.1: 83 percent / sodium hydroxide; tetrabutylammonium bromide / toluene; H₂O / 0.67 h / 100 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; diphenylphosphoranyl azide; tetrabutylammomium bromide; sodium methylate; potassium hexamethylsilazane; L-Selectride; toluene-4-sulfonic acid; acetic acid; triethylamine; orthoformic acid triethyl ester; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; 7.1: Mitsunobu coupling;
DOI:10.1021/ja027882h

Reference yield:

: 16239-18-2
1,6-dibromo-2-naphthol

: 470465-24-8
N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: K₂CO₃ / dimethylformamide / 3 h / 20 °C

2.1: 89 percent / 2,4,6-collidine; copper(I)iodide / methanol / 19 h / Heating

3.1: 76 percent / Na; EtOH / Heating

4.1: 39.0 g / sodium methoxide / methanol / 2 h / Heating

5.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

5.2: 80 percent / tetrahydrofuran; hexane / 1 h / 20 °C

6.1: 43 percent / p-toluenesulfonic acid monohydrate; triethyl orthoformate / CH₂Cl₂ / 19 h / 25 °C

7.1: 77 percent / potassium bis(trimethylsilyl)amide / diethyl ether; toluene / 2 h / 20 °C

8.1: 80 percent / aq. AcOH / 4 h / Heating

9.1: 97 percent / L-selectride / tetrahydrofuran / 17 h / 0 °C

10.1: diphenylphosphoryl azide; diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 17 h / 20 °C

11.1: LiAlH₄ / ethanol; diethyl ether / 2 h / 20 °C

12.1: 528 mg / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

13.1: 83 percent / sodium hydroxide; tetrabutylammonium bromide / toluene; H₂O / 0.67 h / 100 °C

With 2,4,6-trimethyl-pyridine; dmap; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; ethanol; diphenylphosphoranyl azide; tetrabutylammomium bromide; sodium methylate; sodium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; orthoformic acid triethyl ester; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Ullman coupling / 10.1: Mitsunobu coupling;
DOI:10.1021/ja027882h