(3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide

Base Information

• Chemical Name: (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide
• CAS No.: 1301743-49-6
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 1301743-49-6.mol

Synonyms:(3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide

Chemical Property of (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide

There total 2 articles about (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide 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: 95.0%

(6S,7R)-methyl 6-hydroxy-7-(4-methoxyphenyl)-8-nitro-4-oxooctanoate (1301743-48-5) → (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide (1301743-49-6)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 3h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201100125

Reference yield:

methyl 3-(2-((2S, 3R)-2-hydroxy-3-(4-methoxyphenyl)-4-nitrobutyl)-1,3-dioxolan-2-yl)propanoate (1301743-54-3) → (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide (1301743-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; water / 0 - 20 °C

2: ammonium chloride; zinc / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; ammonium chloride; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1002/ejoc.201100125

Reference yield: 83.0%

(3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide (1301743-49-6) → methyl 3-((2R,4S,5S)-4-hydroxy-5-(4-methoxyphenyl)-N-hydroxypiperidin-2-yl)propanoate (1301743-50-9)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at 0 ℃; for 1h; stereoselective reaction;

DOI:10.1002/ejoc.201100125

upstream raw materials:

methyl 3-(2-((2S, 3R)-2-hydroxy-3-(4-methoxyphenyl)-4-nitrobutyl)-1,3-dioxolan-2-yl)propanoate

(6S,7R)-methyl 6-hydroxy-7-(4-methoxyphenyl)-8-nitro-4-oxooctanoate

Downstream raw materials:

(8aS)-6-(4-methoxyphenyl)-7-methyl-1,2,3,5,8,8a-hexahydroindolizine

(S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine

(6R,7S,8aS)-octahydro-6-(4-methoxyphenyl)indolizin-7-ol

(6R,8aS)-hexahydro-6-(4-methoxyphenyl)indolizine-3,7-dione