tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

Base Information

Chemical Name:tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate
CAS No.:151294-66-5
Molecular Formula:C₂₅H₃₃NO₂
Molecular Weight:379.543
Hs Code.:

Synonyms:tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

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Chemical Property of tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

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Technology Process of tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

There total 5 articles about tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-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: 87.0%

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

: 27784-73-2
tert-butyl cyclopentene-1-carboxylate

: 151294-66-5
tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

: tert-butyl (1S,2S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

tert-butyl cyclopentene-1-carboxylate; In tetrahydrofuran; hexane; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane; optical yield given as %de;
DOI:10.1016/j.tetasy.2010.06.001

Reference yield:

: 3400-45-1
cyclopentanecarboxylic acid

: 151294-66-5
tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 13.5 g / conc. H₂SO₄ / CH₂Cl₂ / 20 h / -78 deg C to room temperature

2: 1.) LDA, I₂, 2.) DBU / 1.) THF, -78 deg C, 1.5 h, 2.) 0 deg C, 1 h, room temperature, 48 h

3: 2.) 2,6-di-tert-butylphenol / 1.) toluene, -78 deg C, 2.) THF, -78 deg C to room temperature, 30 min

With 2,6-di-tert-butylphenol; sulfuric acid; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In dichloromethane;
DOI:10.1039/P19940001411

Reference yield:

: 87661-18-5
1,1-dimethylethyl cyclopentanecarboxylate

: 151294-66-5
tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LDA, I₂, 2.) DBU / 1.) THF, -78 deg C, 1.5 h, 2.) 0 deg C, 1 h, room temperature, 48 h

2: 2.) 2,6-di-tert-butylphenol / 1.) toluene, -78 deg C, 2.) THF, -78 deg C to room temperature, 30 min

With 2,6-di-tert-butylphenol; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide;
DOI:10.1039/P19940001411