(S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 627862-69-5
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417
• Mol file: 627862-69-5.mol

Synonyms:(S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 15 articles about (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 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: 90.0%

1-(2-hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (740817-44-1) → (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (627862-69-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/chem.200306039

Reference yield:

rac-O-triisopropylsilyl-2-(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-yl)ethanol (627862-88-8) → (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (627862-69-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaHCO₃ / 3.5 h / Heating

2: 11.6 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.17 h / 25 °C

3: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 3: Dess-Martin oxidation;

DOI:10.1002/chem.200306039

Reference yield:

O-triisopropylsilyl-2-(6,7-dimethoxy-3,4-dihydro-isoquinoline-1-yl)ethanol (627862-66-2) → (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (627862-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / triethylamine; 1,2-(R,R)-N-tosyl-1,2-diphenylethylenediamine; formic acid / dichloro(p-cymene)ruthenium(II) / dimethylformamide / 0 - 25 °C

With formic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200351129

upstream raw materials:

1-(2-hydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

2-(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-yl)ethanol

ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-ylidene)acetic acid ethyl ester

Downstream raw materials:

1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline