methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

Base Information

Chemical Name:methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate
CAS No.:1448055-20-6
Molecular Formula:C₂₃H₂₇NO₂
Molecular Weight:349.473
Hs Code.:

Synonyms:methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

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Chemical Property of methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

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Technology Process of methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

There total 5 articles about methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-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: 77.0%

: 1448055-16-0
methyl (2R,3S,2'R,αS,E)-2-(but-3'-en-2'-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate

: 1448055-20-6
methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 24h;
DOI:10.1039/c3cc43250e

Reference yield:

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 1448055-20-6
methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 20 °C

3.2: 0 - 20 °C

4.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.25 h / -78 °C

4.2: 1 h / Reflux

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C

6.1: Grubbs catalyst first generation / dichloromethane / 24 h / 40 °C

With Grubbs catalyst first generation; n-butyllithium; chloro-trimethyl-silane; oxalyl dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; 4.2: |Claisen-Ireland Rearrangement / 6.1: |Grubbs Olefin Metathesis;
DOI:10.1039/c3cc43250e

Reference yield:

: (Z)-but-2'-en-1'-yl (3R,αS,E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate

: 1448055-20-6
methyl (1R,2S,5R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.25 h / -78 °C

1.2: 1 h / Reflux

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C

3.1: Grubbs catalyst first generation / dichloromethane / 24 h / 40 °C

With Grubbs catalyst first generation; chloro-trimethyl-silane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1.2: |Claisen-Ireland Rearrangement / 3.1: |Grubbs Olefin Metathesis;
DOI:10.1039/c3cc43250e