(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:303043-27-8
Molecular Formula:C₄₃H₅₅NO₁₀
Molecular Weight:745.91
Hs Code.:

(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

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

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

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

There total 16 articles about (3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-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: 96.0%

: 67-56-1
methanol

: 303043-26-7
(3R,4R,5S)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(4-methoxy-naphthalen-2-ylmethoxy)-5-[(2R)-oxiranylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

: 303043-27-8
(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium methylate; In N,N-dimethyl-formamide; at 20 ℃; for 9h;
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

: 303043-27-8
(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 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

7.1: 100 percent / K₂CO₃ / dimethylformamide / 21 h / 120 °C

8.1: 95 percent / NaH / dimethylformamide / 1.5 h / 20 °C

9.1: 100 percent / HCl / methanol / 1 h / 20 °C

10.1: 87 percent / aq. NaHCO₃ / dioxane / 1 h / 20 °C

11.1: 72 percent / pyridine / 0.25 h / 20 °C

12.1: 98 percent / aq. NaOH / dimethylsulfoxide / 1 h / 20 °C

13.1: 96 percent / NaOMe / dimethylformamide / 9 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; borane-THF; hydrogen bromide; hydrogen; bromine; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; phenyllithium; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
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

: 303043-27-8
(3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

5.1: 100 percent / K₂CO₃ / dimethylformamide / 21 h / 120 °C

6.1: 95 percent / NaH / dimethylformamide / 1.5 h / 20 °C

7.1: 100 percent / HCl / methanol / 1 h / 20 °C

8.1: 87 percent / aq. NaHCO₃ / dioxane / 1 h / 20 °C

9.1: 72 percent / pyridine / 0.25 h / 20 °C

10.1: 98 percent / aq. NaOH / dimethylsulfoxide / 1 h / 20 °C

11.1: 96 percent / NaOMe / dimethylformamide / 9 h / 20 °C

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