3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

Base Information

Chemical Name:3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate
CAS No.:1258222-66-0
Molecular Formula:C₁₉H₂₀BrNO₆
Molecular Weight:438.275
Hs Code.:

Synonyms:3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

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Chemical Property of 3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

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Technology Process of 3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

There total 2 articles about 3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate 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: 99.0%

: 1104643-40-4
tert-butyl 2-cyano-2-(p-bromophenyl)acetate

: 762-42-5
dimethyl acetylenedicarboxylate

: 1258222-66-0
3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

Guidance literature:: With [(η6-C6Me6)Ir((S,S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine)]; In toluene; at 0 ℃; for 24.3333h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1246/bcsj.20110307

Reference yield:

: 1116-98-9
cyanoacetic acid tert-butyl ester

: 1633-33-6
4-bromobenzoic anhydride

: 1258222-66-0
3-tert-butyl 1,2-dimethyl (1Z,3S)-3-(4-bromophenyl)-3-cyanoprop-1-ene-1,2,3-tricarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.75 h / -45 °C / Inert atmosphere

1.2: 1 h / -45 °C / Inert atmosphere

2.1: [(η6-C6Me6)Ir((S,S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine)] / toluene / 24.33 h / 0 °C / Inert atmosphere

With [(η6-C6Me6)Ir((S,S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine)]; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; toluene;
DOI:10.1246/bcsj.20110307