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

Base Information

• Chemical Name: [1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine
• CAS No.: 870282-77-2
• Molecular Formula: C₁₅H₂₂N₂O₃
• Molecular Weight: 278.351
• Mol file: 870282-77-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 1 articles about [1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine 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: 100.0%

(R)-1-Amino-2-(methoxymethyl)pyrrolidine (72748-99-3,187035-29-6) + 3,4-dimethoxy-benzaldehyde (120-14-9) → [1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine (870282-77-2)

Guidance literature:

In diethyl ether; at 0 - 20 ℃;

DOI:10.1021/jo051554t

Reference yield: 54.0%

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine (870282-77-2) + N,N-diethyl-2,3-dimethoxy-6-methyl-benzamide (70945-99-2) → (3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-2-((2R)-2-methoxymethylpyrrolidin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one (870282-78-3)

Guidance literature:

N,N-diethyl-2,3-dimethoxy-6-methyl-benzamide; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 - -40 ℃;

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine; With trimethylaluminum; In various solvents; at -40 ℃; for 17h;

DOI:10.1021/jo051554t

Reference yield:

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine (870282-77-2) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: Raney nickel W₂; hydrogen / ethanol / 22 h / Heating

With borane-THF; N,N,N,N,-tetramethylethylenediamine; Raney nickel W₂; hydrogen; sec.-butyllithium; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; toluene; 3.1: Michael reaction / 4.1: Pummerer reaction;

DOI:10.1021/jo051554t

upstream raw materials:

(R)-1-Amino-2-(methoxymethyl)pyrrolidine

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

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

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

2-[(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-ethanol

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

Refernces