(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

Base Information

Chemical Name:(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate
CAS No.:1333429-79-0
Molecular Formula:C₂₅H₂₅ClN₂O₅
Molecular Weight:468.937
Hs Code.:

Synonyms:(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

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Chemical Property of (2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

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Technology Process of (2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

There total 5 articles about (2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate 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: 80.0%

: 102-96-5
(2-nitroethenyl)benzene

: 1333429-64-3
(E)-tert-butyl 5-chloro-2-methyl-3-(3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate

: tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

: 1333429-79-0
(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

Guidance literature:: With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid; In toluene; at 70 ℃; for 40h; optical yield given as %de; stereoselective reaction;
DOI:10.1021/ja206517s

Reference yield:

: 1333429-75-6
C₁₅H₁₆ClNO₃

: tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

: 1333429-79-0
(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C

1.2: 4 h / 0 °C

2.1: diisobutylaluminium hydride / n-heptane; toluene / 3.33 h / -78 °C

3.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid / toluene / 40 h / 70 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; n-butyllithium; diisobutylaluminium hydride; benzoic acid; In tetrahydrofuran; hexane; n-heptane; toluene; 1.1: Wittig reaction / 1.2: Wittig reaction / 3.1: Diels-Alder reaction;
DOI:10.1021/ja206517s

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

: 1333429-79-0
(2S,3S,4S)-tert-butyl 6-chloro-3-nitro-4-(2-oxoethyl)-2-phenyl-3,4-dihydro-1H-carbazole-9(2H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap / acetonitrile / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 4 h / 0 °C

3.1: diisobutylaluminium hydride / n-heptane; toluene / 3.33 h / -78 °C

4.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid / toluene / 40 h / 70 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; dmap; n-butyllithium; diisobutylaluminium hydride; benzoic acid; In tetrahydrofuran; hexane; n-heptane; toluene; acetonitrile; 2.1: Wittig reaction / 2.2: Wittig reaction / 4.1: Diels-Alder reaction;
DOI:10.1021/ja206517s