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

Base Information

Chemical Name: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
CAS No.:1605312-95-5
Molecular Formula:C₂₈H₃₆BrN₃O₅
Molecular Weight:574.515
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 37.0%

: 675109-26-9
6-bromo-1-oxo-2,3-dihydro-1H-isoindole

: 1605312-94-4
(2R,5R)-5-chloromethyl-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

: 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

Guidance literature:: 6-bromo-1-oxo-2,3-dihydro-1H-isoindole; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h;

(2R,5R)-5-chloromethyl-4-(2,4-dimethoxy-benzyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester; With potassium iodide; In N,N-dimethyl-formamide; mineral oil; at 80 ℃; for 3h;
DOI:10.1021/acs.jmedchem.8b00900

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

With sodium tris(acetoxy)borohydride; sodium hydride; methanesulfonyl chloride; triethylamine; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00900

Reference yield:

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 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

Guidance literature:: Multi-step reaction with 3 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

With sodium tris(acetoxy)borohydride; sodium hydride; methanesulfonyl chloride; triethylamine; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00900