(3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol

Base Information

• Chemical Name: (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol
• CAS No.: 865476-82-0
• Molecular Formula: C₂₄H₂₈N₂O₃
• Molecular Weight: 392.498
• Mol file: 865476-82-0.mol

Synonyms:(3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol

Chemical Property of (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol

There total 5 articles about (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-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:

C16H17NO3 + phenethylamine (64-04-0) → (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol (865476-82-0)

Guidance literature:

With lithium perchlorate; In 1,4-dioxane; for 12h; enantiospecific reaction; Reflux;

DOI:10.1016/j.jbc.2021.100535

Reference yield:

(3R,4S)-3,4-epoxy-7-hydroxymethyl-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol + phenethylamine (64-04-0) → (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol (865476-82-0)

Guidance literature:

In propan-1-ol; for 5h; Reflux;

Reference yield:

C15H15NO2 → (3R,4S)-7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol (865476-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid; sodium persulfate / water / 12 h / 130 °C

2: 1-methyl-1H-imidazole; sodium hypochlorite / ethyl acetate; water / 24 h / 20 °C

3: lithium perchlorate / 1,4-dioxane / 12 h / Reflux

With 1-methyl-1H-imidazole; sodium hypochlorite; sodium persulfate; lithium perchlorate; toluene-4-sulfonic acid; In 1,4-dioxane; water; ethyl acetate;

DOI:10.1016/j.jbc.2021.100535

upstream raw materials:

phenethylamine

2,2,9-trimethyl-2H-pyrano[2,3-g]quinoline

1,1-diethoxy-3-methyl-2-butene