2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide

Base Information

• Chemical Name: 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide
• CAS No.: 1277187-90-2
• Molecular Formula: C₂₅H₂₅NO₄
• Molecular Weight: 403.478
• Mol file: 1277187-90-2.mol

Synonyms:2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide

Chemical Property of 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide

There total 7 articles about 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide 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: 97.0%

2-(benzo[d][1,3]dioxol-5-yl)-N-methylethan-1-amine (451-77-4) + 2-(3-(benzyloxy)phenyl)acetyl chloride (59756-83-1) → 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide (1277187-90-2)

Guidance literature:

With sodium hydroxide; In chloroform; water; at 0 - 20 ℃; for 17h;

DOI:10.1002/anie.201006268

Reference yield:

3,4-methylenedioxyphenylacetyl chloride (6845-81-4) → 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide (1277187-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / dichloromethane; water / 16 h / 0 - 20 °C

2.1: borane-THF / tetrahydrofuran / 18 h / Reflux; Inert atmosphere

2.2: 0.5 h / 20 °C

3.1: sodium hydroxide / chloroform; water / 17 h / 0 - 20 °C

With borane-THF; sodium hydroxide; In tetrahydrofuran; dichloromethane; chloroform; water;

DOI:10.1002/anie.201006268

Reference yield:

(3,4-methylenedioxy)phenyl-N-methylacetamide (127901-41-1) → 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide (1277187-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: borane-THF / tetrahydrofuran / 18 h / Reflux; Inert atmosphere

1.2: 0.5 h / 20 °C

2.1: sodium hydroxide / chloroform; water / 17 h / 0 - 20 °C

With borane-THF; sodium hydroxide; In tetrahydrofuran; chloroform; water;

DOI:10.1002/anie.201006268

upstream raw materials:

1,3-benzodioxole-5-acetic acid

3,4-methylenedioxyphenylacetyl chloride

(3,4-methylenedioxy)phenyl-N-methylacetamide

m-hydroxyphenylacetic acid

Downstream raw materials:

1-(3-hydroxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

1-(3-benzyloxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(R)-1-(3-hydroxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(S)-9-hydroxy-2,3-methylenedioxyberbine

Refernces

• 1、 Schrittwieser, Joerg H.,Resch, Verena,Wallner, Silvia,Lienhart, Wolf-Dieter,Sattler, Johann H.,Resch, Jasmin,MacHeroux, Peter,Kroutil, Wolfgang. "Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids". . p. 6703 - 6714. Retrieved 2011/10/18.