tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate
CAS No.:1176327-07-3
Molecular Formula:C₂₀H₃₀BrNO₄
Molecular Weight:428.366
Hs Code.:

Synonyms:tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

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Chemical Property of tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

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Technology Process of tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

There total 9 articles about tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]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: 100.0%

: 1176327-13-1
tert-Butyl 4-(3-bromo-5-hydroxybenzyl)piperidine-1-carboxylate

: 6482-24-2
2-Bromoethyl methyl ether

: 1176327-07-3
tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

Guidance literature:: tert-Butyl 4-(3-bromo-5-hydroxybenzyl)piperidine-1-carboxylate; 2-Bromoethyl methyl ether; With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 8h;

2-Bromoethyl methyl ether; In N,N-dimethyl-formamide;

Reference yield: 98.0%

: 1176327-06-2
tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzylidene]piperidine-1-carboxylate

: 1176327-07-3
tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

Guidance literature:: With hydrogen; 5% rhodium-on-charcoal; In ethyl acetate; at 20 ℃; for 26h; under 760.051 Torr;

Reference yield:

: 626-41-5
3,5-dibromophenol

: 1176327-07-3
tert-butyl 4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 9 h / 80 °C / Inert atmosphere

2.1: n-butyllithium; butyl magnesium bromide / toluene; tetrahydrofuran; hexane / 3 h / 0 °C / Inert atmosphere

2.2: 2.67 h / 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate; methanol / 3 h / 20 °C / Inert atmosphere

4.1: trimethylamine hydrochloride; triethylamine / toluene / 2.5 h / 0 °C / Inert atmosphere

5.1: lithium bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

6.1: toluene / 7 h / Inert atmosphere; Reflux

7.1: potassium carbonate / isopropyl alcohol / 10 h / Reflux; Inert atmosphere

8.1: hydrogen; 5% rhodium-on-charcoal / ethyl acetate / 26 h / 20 °C

With methanol; sodium tetrahydroborate; n-butyllithium; 5% rhodium-on-charcoal; hydrogen; butyl magnesium bromide; trimethylamine hydrochloride; potassium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 7.1: |Wittig Olefination;
DOI:10.1016/j.bmc.2018.02.008