(3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester
• CAS No.: 89877-49-6
• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.364

Synonyms:(3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester

Chemical Property of (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester

There total 6 articles about (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester 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: 94.9%

triethyloxonium fluoroborate (368-39-8) + (3aS,7aR)-2,3,5-Trioxo-7a-phenyl-1,2,3,4,5,7a-hexahydro-indole-3a-carboxylic acid ethyl ester (140700-55-6) → (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester (89877-49-6)

Guidance literature:

In dichloromethane; for 15h; Ambient temperature;

DOI:10.1248/cpb.40.36

Reference yield: 69.0%

(1R,5S,7R)-7-((E)-2-Methoxy-vinyl)-3,4-dioxo-1-phenyl-7-trimethylsilanyloxy-2-aza-bicyclo[3.2.0]heptane-5-carboxylic acid ethyl ester (88461-24-9,140851-98-5) → (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester (89877-49-6) + (1R,2S,3S,6S,7R)-4-Ethoxy-3-hydroxy-2-methoxy-9-oxo-6-phenyl-5-aza-tricyclo[4.3.0.03,7]non-4-ene-7-carboxylic acid ethyl ester (89899-37-6)

Guidance literature:

With triethyloxonium fluoroborate; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1248/cpb.40.36

Reference yield:

3-ethoxycarbonyl-2-phenyldioxopyrroline (59046-34-3) → (3aS,7aR)-2-Ethoxy-3,5-dioxo-7a-phenyl-3,4,5,7a-tetrahydro-indole-3a-carboxylic acid ethyl ester (89877-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 1,2-dimethoxy-ethane / 0 °C / Irradiation

2: 69 percent / Et₃OBF₄ / CH₂Cl₂ / 15 h / Ambient temperature

With triethyloxonium fluoroborate; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1248/cpb.40.36

upstream raw materials:

triethyloxonium fluoroborate

(3aS,7aR)-2,3,5-Trioxo-7a-phenyl-1,2,3,4,5,7a-hexahydro-indole-3a-carboxylic acid ethyl ester

(1R,5S,7R)-7-((E)-2-Methoxy-vinyl)-3,4-dioxo-1-phenyl-7-trimethylsilanyloxy-2-aza-bicyclo[3.2.0]heptane-5-carboxylic acid ethyl ester

3-ethoxycarbonyl-2-phenyldioxopyrroline

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