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

Base Information

Chemical Name:(3R,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidin-3-ol
CAS No.:303043-17-6
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

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

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Chemical Property of (3R,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidin-3-ol

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Technology Process of (3R,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidin-3-ol

There total 5 articles about (3R,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidin-3-ol 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%

: 303043-16-5
(3R,4R,5S)-4-(4-Benzyloxy-phenyl)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1-((R)-1-phenyl-ethyl)-piperidin-3-ol

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

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 23h;
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

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

Guidance literature:: Multi-step reaction with 3 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

With borane-THF; hydrogen; sodium hydride; palladium on activated charcoal; In 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

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

Guidance literature:: Multi-step reaction with 5 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

With borane-THF; hydrogen bromide; hydrogen; bromine; sodium hydride; 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