4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione

Base Information

• Chemical Name: 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione
• CAS No.: 1310549-01-9
• Molecular Formula: C₂₁H₂₃FN₂O₄S
• Molecular Weight: 418.489

Synonyms:4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione

Chemical Property of 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione

Chemical Property:

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Technology Process of 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione

There total 3 articles about 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione 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: 44.0%

1-ethylsulfinylacetylazepan-2-one (221444-85-5) + 1-((4-fluorophenyl)methyl)-1H-pyrrole-2,5-dione → 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione (1310549-01-9)

Guidance literature:

With acetic anhydride; toluene-4-sulfonic acid; In toluene; for 1h; Reflux;

DOI:10.1016/j.bmcl.2011.03.047

Reference yield:

para-fluorobenzylamine (140-75-0) → 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione (1310549-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 20 °C / Reflux

2: acetic anhydride; toluene-4-sulfonic acid / toluene / 1 h / Reflux

With acetic anhydride; toluene-4-sulfonic acid; In acetic acid; toluene; 2: Pummerer cyclization deprotonation cycloaddition;

DOI:10.1016/j.bmcl.2011.03.047

Reference yield:

1-ethylsulfenylacetylazepan-2-one (221444-88-8) → 4-(ethylthio)-2-(4-fluorobenzyl)hexahydro-4,11a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H,11bH)-trione (1310549-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate

2: acetic anhydride; toluene-4-sulfonic acid / toluene / 1 h / Reflux

With sodium periodate; acetic anhydride; toluene-4-sulfonic acid; In toluene; 2: Pummerer cyclization deprotonation cycloaddition;

DOI:10.1016/j.bmcl.2011.03.047

upstream raw materials:

para-fluorobenzylamine

1-ethylsulfenylacetylazepan-2-one

1-ethylsulfinylacetylazepan-2-one

Downstream raw materials:

2-(4-fluorobenzyl)-4-hydroxy-8,9,10,11-tetrahydro-1H-pyrrolo[3',4':3,4]pyrido[1,2-a]azepine-1,3,5(2H,7H)-trione

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