(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

Base Information

Chemical Name:(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate
CAS No.:357608-39-0
Molecular Formula:C₂₃H₂₈BrNO₄
Molecular Weight:462.384
Hs Code.:

Synonyms:(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

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Chemical Property of (R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

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Technology Process of (R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

There total 10 articles about (R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-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: 86.0%

: 357608-38-9
(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylate

: 357608-39-0
(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol016092u

Reference yield:

: 67963-68-2
t-butyldimethylsilyl-4-bromophenol

: 357608-39-0
(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / various solvent(s); tetrahydrofuran / 0.5 h / -78 °C

1.2: 92 percent / tetrahydrofuran; various solvent(s) / -78 - 20 °C

2.1: 52 percent / Na₂CO₃; LiCl / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 2 h / Heating

3.1: 92 percent / AD-mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

4.1: TBAF / tetrahydrofuran / 0 - 20 °C

5.1: 1.10 g / Raney Ni / ethanol / 4 h / Heating

6.1: 90 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

7.1: NaH / tetrahydrofuran / 1 h / 20 °C

7.2: 67 percent / tetrahydrofuran / 20 - 50 °C

8.1: 86 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; methanesulfonamide; tetrabutyl ammonium fluoride; sodium hydride; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nickel; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; tert-butyl alcohol; 3.1: Sharpless dihydroxylation;
DOI:10.1021/ol016092u

Reference yield:

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 357608-39-0
(R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran; petroleum ether / 0.33 h / -78 °C

1.2: 91 percent / tetrahydrofuran; petroleum ether / 3.5 h / 0 °C

2.1: 52 percent / Na₂CO₃; LiCl / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 2 h / Heating

3.1: 92 percent / AD-mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

4.1: TBAF / tetrahydrofuran / 0 - 20 °C

5.1: 1.10 g / Raney Ni / ethanol / 4 h / Heating

6.1: 90 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

7.1: NaH / tetrahydrofuran / 1 h / 20 °C

7.2: 67 percent / tetrahydrofuran / 20 - 50 °C

8.1: 86 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; tetrabutyl ammonium fluoride; sodium hydride; sodium carbonate; lithium chloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nickel; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; Petroleum ether; tert-butyl alcohol; 3.1: Sharpless dihydroxylation;
DOI:10.1021/ol016092u