(3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one

Base Information

• Chemical Name: (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one
• CAS No.: 1429924-70-8
• Molecular Formula: C₂₄H₃₂N₂O₅S
• Molecular Weight: 460.594

Synonyms:(3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one

Chemical Property of (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one

Chemical Property:

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Technology Process of (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one

There total 8 articles about (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-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: 57.0%

(3aR,4R,7R,7aR)-4-allyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one? (1429924-75-3) + ethyl iodide (75-03-6) → (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one (1429924-70-8)

Guidance literature:

(3aR,4R,7R,7aR)-4-allyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one?; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

ethyl iodide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201200376

Reference yield:

(1S,3R,4R,6R,8R,9R,12R)-9-allyl-6-methoxy-12-(pent-4-en-1-yl)-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodecan-10-one (1429924-71-9) → (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one (1429924-70-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile; water / 4 h / 20 °C

2.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: ammonium cerium (IV) nitrate / acetonitrile; water / 5 h / 20 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene; 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; di-isopropyl azodicarboxylate; sodium tris(acetoxy)borohydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1002/chem.201200376

Reference yield:

N-(2-{(1R,2R,5R,6S)-2-allyl-6-[(1R,2R)-2-hydroxy-1,2-diphenylethoxy]-3-oxo-5-(pent-4-en-1-yl)cyclohexyl}ethyl)-N-(4-methoxybenzyl)-2-nitrobenzenesulfonamide (1429924-73-1) → (3aR,4R,6R,7R,7aR)-4-allyl-6-ethyl-1-[(2-nitrophenyl)sulfonyl]-7-(pent-4-en-1-yl)hexahydro-1H-indol-5(6H)-one (1429924-70-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonium cerium (IV) nitrate / acetonitrile; water / 5 h / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene; 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; di-isopropyl azodicarboxylate; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; water; toluene; acetonitrile;

DOI:10.1002/chem.201200376

upstream raw materials:

(1S,3R,4R,6R,8R,9R,12R)-9-allyl-6-methoxy-12-(pent-4-en-1-yl)-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodecan-10-one

2-{(1R,2R,5R,6S)-2-allyl-6-[(1R,2R)-2-hydroxy-1,2-diphenylethoxy]-3-oxo-5-(pent-4-en-1-yl)cyclohexyl}acetaldehyde

N-(2-{(1R,2R,5R,6S)-2-allyl-6-[(1R,2R)-2-hydroxy-1,2-diphenylethoxy]-3-oxo-5-(pent-4-en-1-yl)cyclohexyl}ethyl)-N-(4-methoxybenzyl)-2-nitrobenzenesulfonamide

N-{2-[(1R,2R,5R,6S)-2-allyl-6-hydroxy-3-oxo-5-(pent-4-en-1-yl)cyclohexyl]ethyl}-2-nitrobenzenesulfonamide

Downstream raw materials:

methyl 4-{(3aR,4R,6R,7R,7aR)-6-ethyl-4-(2-methoxy-2-oxoethyl)-1-[(2-nitrophenyl)sulfonyl]-5-oxo-octahydro-1H-indol-7-yl}butanoate

C₂₂H₂₈N₂O₇S

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