(S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate

Base Information

• Chemical Name: (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate
• CAS No.: 956469-18-4
• Molecular Formula: C₃₈H₄₄N₂O₅
• Molecular Weight: 608.778
• Mol file: 956469-18-4.mol

Synonyms:(S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate

Chemical Property of (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate

There total 5 articles about (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate 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-iodo-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (956469-14-0) → (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate (956469-18-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 78.4 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / 0 °C

2: 80.3 percent / PBr₃ / CH₂Cl₂ / 0.67 h / 0 °C

3: 97 percent / cinchona alkaloid-derived quaternary ammonium salt; aq. KOH / CH₂Cl₂; toluene / 8 h / 0 °C

4: 90 percent / K₂CO₃ / Pd(OAc)2 / dimethylformamide; H₂O / 2 h / 90 °C

With potassium hydroxide; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 4: Heck reaction;

DOI:10.1021/jo071162h

Reference yield:

3-hydroxymethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester (956469-15-1) → (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate (956469-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.3 percent / PBr₃ / CH₂Cl₂ / 0.67 h / 0 °C

2: 97 percent / cinchona alkaloid-derived quaternary ammonium salt; aq. KOH / CH₂Cl₂; toluene / 8 h / 0 °C

3: 90 percent / K₂CO₃ / Pd(OAc)2 / dimethylformamide; H₂O / 2 h / 90 °C

With potassium hydroxide; phosphorus tribromide; potassium carbonate; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 3: Heck reaction;

DOI:10.1021/jo071162h

Reference yield:

3-bromomethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester (956469-16-2) → (S,E)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate (956469-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / cinchona alkaloid-derived quaternary ammonium salt; aq. KOH / CH₂Cl₂; toluene / 8 h / 0 °C

2: 90 percent / K₂CO₃ / Pd(OAc)2 / dimethylformamide; H₂O / 2 h / 90 °C

With potassium hydroxide; potassium carbonate; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Heck reaction;

DOI:10.1021/jo071162h

upstream raw materials:

4-iodo-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

3-hydroxymethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester

3-bromomethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester

3-methoxycarbonylindole

Downstream raw materials:

(-)-trans-clavicipitic acid