benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

Base Information

Chemical Name:benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate
CAS No.:1300035-41-9
Molecular Formula:C₂₈H₂₉BrClNO₅
Molecular Weight:574.899
Hs Code.:

Synonyms:benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

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Chemical Property of benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

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Technology Process of benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

There total 6 articles about benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-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: 70.0%

: 1300035-33-9
benzyl (S)-N-(1-(2-bromo-5-methoxyphenyl)-3-(3-methoxyphenyl)but-3-en-2-yl)-N-(2-oxoethyl)carbamate

: 1300035-41-9
benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

Guidance literature:: benzyl (S)-N-(1-(2-bromo-5-methoxyphenyl)-3-(3-methoxyphenyl)but-3-en-2-yl)-N-(2-oxoethyl)carbamate; With aluminum (III) chloride; In nitromethane; at -20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In nitromethane;
DOI:10.1021/ol200725m

Reference yield:

: 1300035-74-8
(S)-1-(2-bromo-5-methoxyphenyl)-3-(3-methoxyphenyl)but-3-en-2-amine

: 1300035-41-9
benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: potassium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.75 h / -78 - 20 °C / Inert atmosphere

5.1: aluminum (III) chloride / nitromethane / -20 °C / Inert atmosphere

With pyridine; aluminum (III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; nitromethane; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation;
DOI:10.1021/ol200725m

Reference yield:

: 1300035-27-1
tert-butyl (S)-(1-(2-bromo-5-methoxyphenyl)-3-(3-methoxyphenyl)but-3-en-2-yl)carbamate

: 1300035-41-9
benzyl (2S)-2-(2-bromo-5-methoxybenzyl)-3-chloro-5-hydroxy-3-(3-methoxyphenyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: potassium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.75 h / -78 - 20 °C / Inert atmosphere

6.1: aluminum (III) chloride / nitromethane / -20 °C / Inert atmosphere

With pyridine; aluminum (III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; nitromethane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation;
DOI:10.1021/ol200725m