N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine

Base Information

• Chemical Name: N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine
• CAS No.: 165963-38-2
• Molecular Formula: C₂₃H₂₈N₂O₅S
• Molecular Weight: 444.552

Synonyms:N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine

Chemical Property of N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine

There total 9 articles about N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine 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:

3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (6116-76-3) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine (165963-38-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

2: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, a) -70 deg C, 30 min, b) RT, 18 h

3: 75 percent / NaOH / methanol / 2 h / Heating

4: 80 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

5: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

Reference yield:

1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (144219-62-5) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine (165963-38-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, a) -70 deg C, 30 min, b) RT, 18 h

2: 75 percent / NaOH / methanol / 2 h / Heating

3: 80 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

Reference yield:

ethyl 1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetate (144219-63-6) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine (165963-38-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaOH / methanol / 2 h / Heating

2: 80 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

3: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

upstream raw materials:

morpholine

ethyl 1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetate

benzenesulfonyl chloride

N-(3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)morpholine

Downstream raw materials:

N-<1β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolyl)ethyl>morpholine

N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>morpholine

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