4-Isoquinolinol, 3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-, (3S,4S)-

Base Information

• Chemical Name: 4-Isoquinolinol, 3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-, (3S,4S)-
• CAS No.: 394739-99-2
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 394739-99-2.mol

Synonyms:

Chemical Property of 4-Isoquinolinol, 3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-, (3S,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Isoquinolinol, 3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-, (3S,4S)-

There total 9 articles about 4-Isoquinolinol, 3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-, (3S,4S)- 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:

(S)-[(2,3-Dimethoxy-benzyl)-methyl-amino]-(3,4-dimethoxy-phenyl)-acetaldehyde → (3S,4S)-(+)-7,8-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol (394739-99-2)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200111)2001:22<4343::AID-EJOC4343>3.0.CO;2-D

Reference yield:

(2S)-(+)-3,4-dimethoxyphenylglycine (147383-98-0) → (3S,4S)-(+)-7,8-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol (394739-99-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / LiBH₄; TMSCl / tetrahydrofuran / 25 h / 0 - 20 °C

2: 90 percent / molecular sieves, 4 Angstroem / benzene / 4 h / Heating

3: 90 percent / NaBH₄ / methanol / 3 h / 20 °C

4: 80 percent / NaBH₃CN / acetonitrile; H₂O / 24 h / 0 °C

5: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / 0.75 h / -60 °C

6: HCl / acetone; H₂O / 2 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; lithium borohydride; chloro-trimethyl-silane; molecular sieve; oxalyl dichloride; 4 A molecular sieve; sodium cyanoborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1002/1099-0690(200111)2001:22<4343::AID-EJOC4343>3.0.CO;2-D

Reference yield:

(+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2-(3,4-dimethoxyphenyl)-N-methylacetamide (234089-44-2) → (3S,4S)-(+)-7,8-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol (394739-99-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nBuLi; iPr₂NH / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

1.2: 89 percent / tetrahydrofuran; hexane / 1 h / -105 °C

2.1: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 78 percent / H₂ / Ni/Raney / CH₂Cl₂ / 48 h / 7757.22 Torr

3.1: 86 percent / H₂SO₄; H₂O / dioxane / 6 h / Heating

4.1: 80 percent / LiBH₄; TMSCl / tetrahydrofuran / 25 h / 0 - 20 °C

5.1: 90 percent / molecular sieves, 4 Angstroem / benzene / 4 h / Heating

6.1: 90 percent / NaBH₄ / methanol / 3 h / 20 °C

7.1: 80 percent / NaBH₃CN / acetonitrile; H₂O / 24 h / 0 °C

8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / 0.75 h / -60 °C

9.1: HCl / acetone; H₂O / 2 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; molecular sieve; oxalyl dichloride; 4 A molecular sieve; sulfuric acid; water; sodium cyanoborohydride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1002/1099-0690(200111)2001:22<4343::AID-EJOC4343>3.0.CO;2-D

upstream raw materials:

(+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2-(3,4-dimethoxyphenyl)-N-methylacetamide

(2S)-(+)-3,4-dimethoxyphenylglycine

[2S,1'S,2'S]-(+)-2-amino-2-(3,4-dimethoxyphenyl)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide

[2S,1'S,2'S]-(+)-2-(3,4-dimethoxyphenyl)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide