(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:357608-37-8
Molecular Formula:C₂₅H₄₃NO₄Si
Molecular Weight:449.706
Hs Code.:

Synonyms:(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

There total 8 articles about (3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 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: 90.0%

: 13154-24-0
triisopropylsilyl chloride

: 257938-67-3
tert-butyl (3R,4R)-3-hydroxy-4-(4-hydroxyphenyl)-piperidine-1-carboxylate

: 357608-37-8
(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol016092u

Reference yield:

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

: 357608-37-8
(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; AD-mix-α; n-butyllithium; methanesulfonamide; tetrabutyl ammonium fluoride; 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

: 357608-37-8
(3R,4R)-3-Hydroxy-4-(4-triisopropylsilanyloxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; AD-mix-α; methanesulfonamide; tetrabutyl ammonium fluoride; 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