(13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

Base Information

• Chemical Name: (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine
• CAS No.: 870282-72-7
• Molecular Formula: C₂₇H₂₉NO₄S
• Molecular Weight: 463.598
• Mol file: 870282-72-7.mol

Synonyms:(13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

Chemical Property of (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

There total 6 articles about (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine 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:

(3S)-2-(2-phenylsulfinylethyl)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (870282-71-6) → (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine (870282-72-7)

Guidance literature:

With trifluoroacetic acid; trifluoroacetic anhydride; In toluene; for 15h; Heating;

DOI:10.1021/jo051554t

Reference yield:

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine (870282-77-2) → (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine (870282-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C

1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / Heating

2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating

3.1: 94 percent / methanol / 22 h / Heating

4.1: TFAA; TFA / toluene / 15 h / Heating

With borane-THF; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; hexane; toluene; 3.1: Michael reaction / 4.1: Pummerer reaction;

DOI:10.1021/jo051554t

Reference yield:

(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (870282-79-4) → (13aS)-2,3,9,10-tetramethoxy-5-phenylsulfanyl-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine (870282-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / methanol / 22 h / Heating

2: TFAA; TFA / toluene / 15 h / Heating

With trifluoroacetic acid; trifluoroacetic anhydride; In methanol; toluene; 1: Michael reaction / 2: Pummerer reaction;

DOI:10.1021/jo051554t

upstream raw materials:

(3S)-2-(2-phenylsulfinylethyl)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine

(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-2-((2R)-2-methoxymethylpyrrolidin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one

Downstream raw materials:

tetrahydropalmatine

(R)-(+)-tetrahydropalmatine

Refernces