tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

Base Information

Chemical Name:tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate
CAS No.:816444-24-3
Molecular Formula:C₂₈H₃₉NO₄
Molecular Weight:453.622
Hs Code.:

Synonyms:tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

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Chemical Property of tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

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Technology Process of tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

There total 9 articles about tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate 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: 42.0%

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

: 134430-93-6,308273-67-8,680185-65-3
(R)-N-(3,4-dimethoxybenzyl)-N-(α-methylbenzyl)amine

: 479201-45-1
(+/-)-tert-butyl 3-methylcyclopentene-1-carboxylate

: 816444-24-3
tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

: tert-butyl (αS)-2-[n-benzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

: 479201-50-8
tert-butyl (1R,2S,3R,αS)-3-methyl-2-(N-benzyl-N-α-methylbenzylamino)cyclopentane-1-carboxylate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; (R)-N-(3,4-dimethoxybenzyl)-N-(α-methylbenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(+/-)-tert-butyl 3-methylcyclopentene-1-carboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane; at -78 - 30 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

: 1280736-75-5
C₉H₁₆O₅S

: 816444-24-3
tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 0 °C / Inert atmosphere

2.1: potassium hydroxide / methanol; water / 8 h / 60 °C

2.2: 20 °C / pH 1

3.1: sulfuric acid / dichloromethane; water / 16 h / 0 °C

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

4.2: 3 h / -78 °C / Inert atmosphere

4.3: -78 - 30 °C / Inert atmosphere

With n-butyllithium; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/j.tetasy.2010.12.007

Reference yield:

: 30680-84-3
methyl 1-methyl-2-oxocyclopentane-1-carboxylate

: 816444-24-3
tert-butyl (1S,2R,3S,αR)-2-[N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)-amino]-3-methylcyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: methanol; sodium methylate / 3 h / Reflux; Inert atmosphere

1.2: 3 h / Reflux; Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 9 h / 0 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 0 °C / Inert atmosphere

5.1: potassium hydroxide / methanol; water / 8 h / 60 °C

5.2: 20 °C / pH 1

6.1: sulfuric acid / dichloromethane; water / 16 h / 0 °C

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

7.2: 3 h / -78 °C / Inert atmosphere

7.3: -78 - 30 °C / Inert atmosphere

With methanol; dmap; sodium tetrahydroborate; n-butyllithium; sulfuric acid; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/j.tetasy.2010.12.007