(1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester

Base Information

• Chemical Name: (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester
• CAS No.: 120566-53-2
• Molecular Formula: C₂₀H₂₀Br₂N₂O₃
• Molecular Weight: 496.198

Synonyms:(1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester

Chemical Property of (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester

There total 4 articles about (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester 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: 79.0%

carbon monoxide (201230-82-2) + (1RS,2RS,6SR,7RS,8SR)-7-bromo-3-trifluoromethanesulfonyloxy-1-vinyl-9-azatricyclo[4.4.0.02,8]dec-3-ene-9-carboxylic acid methyl ester (120566-52-1) + 2-bromoaniline (615-36-1) → (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.02,8]dec-3-ene-9-carboxylic acid methyl ester (120566-53-2)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; under 760 Torr;

DOI:10.1016/S0040-4039(00)82114-0

Reference yield:

(1RS,2RS,6SR,7RS,8SR)-7-bromo-3-oxo-1-vinyl-9-azatricyclo[4.4.0.02,8]decane-9-carboxylic acid methyl ester (120566-50-9) → (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.02,8]dec-3-ene-9-carboxylic acid methyl ester (120566-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 0 °C

2.1: 439 mg / Pd(PPh₃)4 / dimethylformamide / 11 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja055711h

Reference yield:

(4aRS,8aSR)-7-oxo-8a-vinyl-4a,5,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid methyl ester (120016-51-5) → (1RS,2SR,6SR,7RS,8SR)-7-bromo-3-(2-bromophenylcarbamoyl)-1-vinyl-9-azatricyclo[4.4.0.02,8]dec-3-ene-9-carboxylic acid methyl ester (120566-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / 1 equiv Br₂, 1,2,2,6-pentamethylpiperidine / 23 °C

2: 85 percent / CF₃COOH / 10 h / Heating

3: 100 percent / LDA / tetrahydrofuran / -78 - 0 °C

4: 79 percent / 1 molpercent Pd(PPh₃)4 / dimethylformamide / 80 °C / 760 Torr

With 1,2,2,6-pentamethylpiperidine; bromine; trifluoroacetic acid; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)82114-0

upstream raw materials:

carbon monoxide

(1RS,2RS,6SR,7RS,8SR)-7-bromo-3-trifluoromethanesulfonyloxy-1-vinyl-9-azatricyclo[4.4.0.0^2,8]dec-3-ene-9-carboxylic acid methyl ester

2-bromoaniline

(1RS,2RS,6SR,7RS,8SR)-7-bromo-3-oxo-1-vinyl-9-azatricyclo[4.4.0.0^2,8]decane-9-carboxylic acid methyl ester

Downstream raw materials:

C₂₇H₂₅BrN₂O₃

C₂₇H₂₅BrN₂O₃

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