(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

Base Information

Chemical Name:(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one
CAS No.:156326-81-7
Molecular Formula:C₂₄H₂₆N₄O₄S
Molecular Weight:466.561
Hs Code.:

Synonyms:(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

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Chemical Property of (+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

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Technology Process of (+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

There total 12 articles about (+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-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:

: 156326-69-1
(+)-(S)-1-Ethyl-2-oxo-3-cyclohexene-1-propanoic acid methyl ester

: 156326-81-7
(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2: 82 percent / N-chlorosuccinimide / CCl₄ / 5 h / 0 °C

3: 80 percent / CH₃ONa / 2 h / Heating

4: 74 percent / 1 N aq. HCl / tetrahydrofuran / 3 h

5: 94 percent / p-TsOH / toluene / 5 h / Heating

6: 84 percent / NaH, CuI / hexamethylphosphoric acid triamide / 2.) 120 deg C, 2 h

7: 1.) 1 N lithium triethylborohydride; 6 N aq. NaOH, 2.) 30percent H₂O₂ / 1.) THF, 1 h; EtOH, 2.) room temp., 15 h

8: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂; tetrahydrofuran / 2 h / 0 °C

9: sodium azide / dimethylformamide / 2 h / 80 °C

10: tetrabutylammonium hydrogenosulfate, 50percent aq. NaOH / CH₂Cl₂ / 2 h

With hydrogenchloride; dmap; sodium hydroxide; N-chloro-succinimide; copper(l) iodide; sodium azide; dihydrogen peroxide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00088a008

Reference yield:

: 156326-78-2
(+)-(S)-1-Ethyl-2,4-dioxocyclohexane-1-propanoic acid methyl ester

: 156326-81-7
(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / p-TsOH / toluene / 5 h / Heating

2: 84 percent / NaH, CuI / hexamethylphosphoric acid triamide / 2.) 120 deg C, 2 h

3: 1.) 1 N lithium triethylborohydride; 6 N aq. NaOH, 2.) 30percent H₂O₂ / 1.) THF, 1 h; EtOH, 2.) room temp., 15 h

4: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂; tetrahydrofuran / 2 h / 0 °C

5: sodium azide / dimethylformamide / 2 h / 80 °C

6: tetrabutylammonium hydrogenosulfate, 50percent aq. NaOH / CH₂Cl₂ / 2 h

With dmap; sodium hydroxide; copper(l) iodide; sodium azide; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00088a008

Reference yield:

: 115867-85-1
(+)-(S)-1-Ethyl-2-oxocyclohexane-1-propanoic acid methyl ester

: 156326-81-7
(+)-(R)-3-(3-Azidopropyl)-3-ethyl-9-<(4-methoxyphenyl)sulfonyl>-1,2,3,9-tetrahydro-4H-carbazol-4-one

Guidance literature:: Multi-step reaction with 12 steps

1: Et₃N / dimethylformamide / 48 h / 100 °C

2: 80 percent / 2,3-dichloro-5,6-dicyanobenzoquinone, 2,6-lutidine / toluene / 96 h / 20 °C

3: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

4: 82 percent / N-chlorosuccinimide / CCl₄ / 5 h / 0 °C

5: 80 percent / CH₃ONa / 2 h / Heating

6: 74 percent / 1 N aq. HCl / tetrahydrofuran / 3 h

7: 94 percent / p-TsOH / toluene / 5 h / Heating

8: 84 percent / NaH, CuI / hexamethylphosphoric acid triamide / 2.) 120 deg C, 2 h

9: 1.) 1 N lithium triethylborohydride; 6 N aq. NaOH, 2.) 30percent H₂O₂ / 1.) THF, 1 h; EtOH, 2.) room temp., 15 h

10: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂; tetrahydrofuran / 2 h / 0 °C

11: sodium azide / dimethylformamide / 2 h / 80 °C

12: tetrabutylammonium hydrogenosulfate, 50percent aq. NaOH / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; N-chloro-succinimide; copper(l) iodide; sodium azide; dihydrogen peroxide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00088a008