N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine

Base Information

• Chemical Name: N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine
• CAS No.: 139259-02-2
• Molecular Formula: C₂₃H₂₁ClN₂O₃
• Molecular Weight: 408.884

Synonyms:N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine

Chemical Property of N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine

Chemical Property:

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Technology Process of N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine

There total 3 articles about N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine 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:

4-chlorobenzaldehyde (104-88-1) → N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine (139259-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2) MgSO₄ / 1) CH₂Cl₂/Et₂O, 2) 15 min

2: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

With magnesium sulfate; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)80309-4

Reference yield:

L-tryptophan methyl ester (4299-70-1) → N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine (139259-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2) MgSO₄ / 1) CH₂Cl₂/Et₂O, 2) 15 min

2: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

With magnesium sulfate; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)80309-4

Reference yield:

danishefsky's diene (54125-02-9) + (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester (139258-97-2) → N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6S)-2,3-didehydro-4-oxo-6- piperidine (139259-08-8) + N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine (139259-02-2)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; dichloromethane; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)80309-4

upstream raw materials:

danishefsky's diene

(S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

4-chlorobenzaldehyde

L-tryptophan methyl ester

Downstream raw materials:

1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine

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