(R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane

Base Information

• Chemical Name: (R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane
• CAS No.: 620158-88-5
• Molecular Formula: C₂₄H₃₂ClNO₅S
• Molecular Weight: 482.041

Synonyms:(R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane

Chemical Property of (R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane

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Technology Process of (R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane

There total 1 articles about (R_S,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane 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: 53.0%

4-chlorobutyl bromide (6940-78-9) + (RS,3R,5S)-(-)-methoxy-N-methyl-3-hydroxy-5-(3,4-dimethoxyphenyl)-5-N-(p-toluenesulfinyl)pentanamide (299210-03-0) → (RS,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane (620158-88-5)

Guidance literature:

4-chlorobutyl bromide; With magnesium; In diethyl ether; at 20 ℃; for 1h;

(R_S,3R,5S)-(-)-methoxy-N-methyl-3-hydroxy-5-(3,4-dimethoxyphenyl)-5-N-(p-toluenesulfinyl)pentanamide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 8h;

DOI:10.1021/ol035390j

Reference yield:

(RS,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane (620158-88-5) → (2S,4R)-6-(4-Chloro-butyl)-2-(3,4-dimethoxy-phenyl)-2,3,4,5-tetrahydro-pyridin-4-ol

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/ol035390j

Reference yield:

(RS,3R,5S)-(-)-1-(3,4-dimethoxyphenyl)-1-(N-p-toluenesulfinyl)amino-3-hydroxy-5-oxo-9-chlorononane (620158-88-5) → (2S,4S,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-ol

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / tetrahydrofuran / 0.25 h / 0 °C

2: 60 percent / DIBAL-H-n-BuLi "ate" complex / diethyl ether; hexane / 20 h / -78 - 10 °C

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ol035390j

upstream raw materials:

4-chlorobutyl bromide

(R_S,3R,5S)-(-)-methoxy-N-methyl-3-hydroxy-5-(3,4-dimethoxyphenyl)-5-N-(p-toluenesulfinyl)pentanamide

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