(1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

Base Information

• Chemical Name: (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one
• CAS No.: 124156-57-6
• Molecular Formula: C₃₀H₄₁N₅O₄
• Molecular Weight: 535.687

Synonyms:

Chemical Property of (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

Chemical Property:

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Technology Process of (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

There total 3 articles about (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one 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-{[1-Methoxycarbonyl-2-(1H-pyrazol-3-yl)-ethylamino]-methyl}-1H-indole-2-carboxylic acid → (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124156-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(dimethylamino)pyridine, 4-methylmorpholine, N-ethyl-N'-<2-(dimethylamino)ethyl>carbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

2: 1.) LiOH 2.) 1-hydroxybenzotriazole, N-ethyl-N'-<3-(diethylamino)propyl>carbodiimide, 4-methylmorpholine / 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight

With 4-methyl-morpholine; dmap; lithium hydroxide; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; benzotriazol-1-ol; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00291a060

Reference yield:

N-<<3-<2-(benzyloxycarbonyl)indolyl>>methyl>-dl-β-4-pyrazolylalanine methyl ester (124175-16-2) → (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124156-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, Pd-C / methanol / 3040 Torr

2: 4-(dimethylamino)pyridine, 4-methylmorpholine, N-ethyl-N'-<2-(dimethylamino)ethyl>carbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

3: 1.) LiOH 2.) 1-hydroxybenzotriazole, N-ethyl-N'-<3-(diethylamino)propyl>carbodiimide, 4-methylmorpholine / 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight

With 4-methyl-morpholine; dmap; lithium hydroxide; palladium on activated charcoal; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; hydrogen; benzotriazol-1-ol; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00291a060

Reference yield:

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride (104882-45-3) + 2-<1-(methoxycarbonyl)-2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydro<3,4-b>indole-3-one (135674-93-0) → (1'R,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124223-58-1) + (1'S,2''S,3''R,4''S)-2-<1--2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124156-57-6)

Guidance literature:

With 4-methyl-morpholine; lithium hydroxide; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; benzotriazol-1-ol; Yield given. Yields of byproduct given; 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight;

DOI:10.1021/jo00291a060

upstream raw materials:

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

2-<1-(methoxycarbonyl)-2-(3-pyrazolyl)ethyl>-1,2,3,4-tetrahydro<3,4-b>indole-3-one

N-<<3-<2-(benzyloxycarbonyl)indolyl>>methyl>-dl-β-4-pyrazolylalanine methyl ester

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