(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester
CAS No.:1605312-96-6
Molecular Formula:C₂₉H₃₆N₄O₅
Molecular Weight:520.629
Hs Code.:

Synonyms:(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

There total 5 articles about (2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl 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: 75.0%

: 557-21-1
zinc(II) cyanide

: 1605312-95-5
tert-butyl (2R,5S)-5-[(6-bromo-1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-4-[(2,4-dimethoxyphenyl)methyl]-2-methylpiperazine-1-carboxylate

: 1605312-96-6
(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; N,N-dimethyl-formamide; at 100 ℃; for 1h;
DOI:10.1021/acs.jmedchem.8b00900

Reference yield:

: 1403898-64-5
(2R,5R)-5-(hydroxymethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester

: 1605312-96-6
(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Cooling with ice

2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / Cooling with ice

3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 20 °C

3.2: 3 h / 80 °C

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide; water / 1 h / 100 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; sodium hydride; methanesulfonyl chloride; triethylamine; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00900

Reference yield:

: 1605312-93-3
(2R,5R)-4-(2,4-dimethoxy-benzyl)-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

: 1605312-96-6
(2R,5S)-5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / Cooling with ice

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 20 °C

2.2: 3 h / 80 °C

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide; water / 1 h / 100 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; methanesulfonyl chloride; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00900