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

Base Information

• Chemical Name: 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine
• CAS No.: 139259-14-6
• Molecular Formula: C₂₃H₂₁ClN₂O₃
• Molecular Weight: 408.884

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

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

Chemical Property:

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

There total 4 articles about 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine 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: 56.0%

N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6R)-2,3-didehydro-4-oxo-6- piperidine (139259-02-2) → 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine (139259-14-6)

Guidance literature:

trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

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

Reference yield:

4-chlorobenzaldehyde (104-88-1) → 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine (139259-14-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

3: 56 percent / CF₃COOH / CH₂Cl₂ / 3 h / Ambient temperature

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

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

Reference yield:

(S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester (139258-97-2) → 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4- quinolizine (139259-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

2: 56 percent / CF₃COOH / CH₂Cl₂ / 3 h / Ambient temperature

With zinc(II) chloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

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

4-chlorobenzaldehyde

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

L-tryptophan methyl ester

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