(2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol

Base Information

• Chemical Name: (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol
• CAS No.: 394740-13-7
• Molecular Formula: C₁₉H₂₃NO₅
• Molecular Weight: 345.395
• Mol file: 394740-13-7.mol

Synonyms:(2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol

Chemical Property of (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol

There total 7 articles about (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol 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: 80.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-methylenedioxyphenyl)ethanol (394740-10-4) → (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol (394740-13-7)

Guidance literature:

With sodium cyanoborohydride; In water; acetonitrile; at 0 ℃; for 24h;

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

Reference yield:

(S)-(+)-3,4-(methylenedioxy)phenylglycine (250666-02-5) → (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol (394740-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / LiBH₄; TMSCl / tetrahydrofuran / 25 h / 0 - 20 °C

2: 85 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

With sodium tetrahydroborate; lithium borohydride; chloro-trimethyl-silane; molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; methanol; water; 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)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide (247118-52-1) → (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol (394740-13-7)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 91 percent / tetrahydrofuran; hexane / 1 h / -105 °C

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

2.2: 79 percent / H₂ / Ni/Raney / CH₂Cl₂ / 48 h / 7757.22 Torr

3.1: 89 percent / H₂SO₄; H₂O / dioxane / 6 h / Heating

4.1: 78 percent / LiBH₄; TMSCl / tetrahydrofuran / 25 h / 0 - 20 °C

5.1: 85 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

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

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

upstream raw materials:

formaldehyd

(2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-methylenedioxyphenyl)ethanol

(S)-(+)-3,4-(methylenedioxy)phenylglycine

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

Downstream raw materials:

(S)-Benzo[1,3]dioxol-5-yl-[(2,3-dimethoxy-benzyl)-methyl-amino]-acetaldehyde