2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

Base Information

• Chemical Name: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-
• CAS No.: 68681-73-2
• Molecular Formula: C17H25 N O3
• Molecular Weight: 291.39
• Mol file: 68681-73-2.mol

Synonyms:2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, [2S-(2a,4b,9aa)]-;(-)-Lasubin II; (-)-Lasubine II; Lasubine II

Chemical Property of 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

There total 106 articles about 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)- 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: 93.0%

(4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (221664-11-5) → (-)-(2S,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine (68681-73-2)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 2h; diastereospecific reaction; Inert atmosphere;

DOI:10.1021/jacs.5b11248

Reference yield: 77.0%

(2S,4S,6S)-(-)-2-(3,4-dimethoxyphenyl)-6-(4-hydroxybutyl)-piperidin-4-ol (263247-25-2) → (-)-(2S,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine (68681-73-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.3987/com-99-s82

Reference yield: 66.0%

(4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one (221664-11-5) → (-)-(2S,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine (68681-73-2) + (2R,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine (386285-44-5)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol3015573

upstream raw materials:

(4S,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one

4-methoxy-3-(trisopropylsilyl)pyridine

4-lithio-1,2-dimethoxybenzene

4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride

Downstream raw materials:

(+)-subcosine I

2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

2-(p-benzyloxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine