(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:303043-18-7
Molecular Formula:C₂₂H₃₃NO₇
Molecular Weight:423.507
Hs Code.:

Synonyms:(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

There total 6 articles about (3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-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: 85.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 303043-17-6
(3R,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidin-3-ol

: 303043-18-7
(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 1h;
DOI:10.1016/S0014-827X(01)01004-7

Reference yield:

: 257928-45-3
(3S)-4-(4-benzyloxy-phenyl)-1-[(1R)-phenyl-ethyl]-1,2,3,6-tetrahydro-pyridin-3-ol

: 303043-18-7
(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 20 °C

1.2: 84 percent / dimethylformamide / 2 h / 20 °C

2.1: BH₃*THF / 1,2-dimethoxy-ethane / 5.5 h / 20 °C

2.2: 74 percent / aq. sodium percarbonate / 1,2-dimethoxy-ethane / 17 h / 50 - 55 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 23 h / 20 °C

4.1: 85 percent / aq. NaHCO₃ / dioxane / 1 h / 20 °C

With borane-THF; hydrogen; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1016/S0014-827X(01)01004-7

Reference yield:

: 257928-43-1
(R)-4-(4-benzyloxy-phenyl)-1-(1-phenyl-ethyl)-1,2,3,6-tetrahydro-pyridine

: 303043-18-7
(3S,4R,5R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. HBr; Br₂ / dioxane / 2.5 h / 3 - 5 °C

1.2: 47 percent / aq. NaOH / 2.5 h / 3 - 5 °C

2.1: 91 percent / PhLi / various solvent(s) / 1.5 h / -15 °C

3.1: NaH / dimethylformamide / 20 °C

3.2: 84 percent / dimethylformamide / 2 h / 20 °C

4.1: BH₃*THF / 1,2-dimethoxy-ethane / 5.5 h / 20 °C

4.2: 74 percent / aq. sodium percarbonate / 1,2-dimethoxy-ethane / 17 h / 50 - 55 °C

5.1: 100 percent / H₂ / Pd/C / methanol / 23 h / 20 °C

6.1: 85 percent / aq. NaHCO₃ / dioxane / 1 h / 20 °C

With borane-THF; hydrogen bromide; hydrogen; bromine; sodium hydride; sodium hydrogencarbonate; phenyllithium; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1016/S0014-827X(01)01004-7