(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

Base Information

Chemical Name:(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one
CAS No.:616890-51-8
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

Synonyms:(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

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Chemical Property of (5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

Chemical Property:

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Technology Process of (5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

There total 8 articles about (5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one 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%

: 616890-50-7
(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

: 616890-51-8
(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jm0302086

Reference yield:

: (2R,3R)-3-(dibenzylamino)-5-(tert-butyldimethylsilyloxy)-2-(methoxymethoxy)pentanal

: 616890-51-8
(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / toluene

1.2: 1.96 g / toluene / 2 h / 0 °C

2.1: H₂ / Pd(OH)2/C / ethanol / 5 h / 20 °C / 760 Torr

3.1: 448 mg / EDCI*HCl / tetrahydrofuran / 4 h

4.1: 50 percent / NaH / dimethylformamide / 5.5 h / 20 °C

5.1: 86 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; 1.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086

Reference yield:

: 616890-45-0
(3S,4R)-4-(dibenzylamino)-6-(tert-butyldimethylsilyloxy)hex-1-en-3-ol

: 616890-51-8
(5S,6R)-N-(p-methoxybenzyl)-6-(2-hydroxyethyl)-5-methoxymethoxypiperidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating

2.1: 81 percent / trimethylamine oxide dihydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

3.1: aq. NaIO₄ / diethyl ether / 3 h / 0 °C

4.1: NaH / toluene

4.2: 1.96 g / toluene / 2 h / 0 °C

5.1: H₂ / Pd(OH)2/C / ethanol / 5 h / 20 °C / 760 Torr

6.1: 448 mg / EDCI*HCl / tetrahydrofuran / 4 h

7.1: 50 percent / NaH / dimethylformamide / 5.5 h / 20 °C

8.1: 86 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium iodide; palladium dihydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086