(6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone

Base Information

• Chemical Name: (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone
• CAS No.: 102734-22-5
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 102734-22-5.mol

Synonyms:(6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone

Chemical Property of (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone

There total 3 articles about (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone 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: 74.0%

(6R*,8S*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone (102652-52-8) → (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone (102734-22-5)

Guidance literature:

With triphenylphosphine; benzoic acid; diethylazodicarboxylate; In dichloromethane; for 48h; Ambient temperature;

Reference yield:

Methyl 4-butanoate (102652-51-7) → (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone (102734-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) (trimethylsilyl)imidazole, 2) 2-pyridinol, 1 M (C₄H₉)4NF in THF / 1) 4 h, CH₂Cl₂, 2) 2 h, 160 deg C

2: 74 percent / triphenylphosphane/benzoic acid/diethyl azodicarboxylate / CH₂Cl₂ / 48 h / Ambient temperature

With 2-hydroxypyridin; tetrabutyl ammonium fluoride; 1-(Trimethylsilyl)imidazole; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In dichloromethane;

Reference yield:

Methyl 4-<2-exo,6-exo-6-(3,4-dimethoxyphenyl)-7-oxa-1-azabicyclo<2.2.1>heptan-2-yl>butanoate (102652-47-1) → (6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone (102734-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Zn(powder)/CH₃COOH(80percent) / 4 h / 65 °C

2: 1) (trimethylsilyl)imidazole, 2) 2-pyridinol, 1 M (C₄H₉)4NF in THF / 1) 4 h, CH₂Cl₂, 2) 2 h, 160 deg C

3: 74 percent / triphenylphosphane/benzoic acid/diethyl azodicarboxylate / CH₂Cl₂ / 48 h / Ambient temperature

With 2-hydroxypyridin; tetrabutyl ammonium fluoride; acetic acid; 1-(Trimethylsilyl)imidazole; triphenylphosphine; benzoic acid; zinc; diethylazodicarboxylate; In dichloromethane;

upstream raw materials:

(6R*,8S*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone

Methyl 4-butanoate

Methyl 4-<2-exo,6-exo-6-(3,4-dimethoxyphenyl)-7-oxa-1-azabicyclo<2.2.1>heptan-2-yl>butanoate

Downstream raw materials:

(±)-lasubine II