(1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone

Base Information

• Chemical Name: (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone
• CAS No.: 234079-72-2
• Molecular Formula: C₂₉H₂₇NO₂
• Molecular Weight: 421.539
• Mol file: 234079-72-2.mol

Synonyms:(1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone

Chemical Property of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone

There total 6 articles about (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone 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: 95.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 1-[(S)-2-(Hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-propenone (153391-00-5) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone (234079-72-2)

Guidance literature:

With diethylaluminium chloride; at -40 ℃; for 10h;

DOI:10.1039/a902535i

Reference yield:

(S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone (234079-72-2)

Guidance literature:

Multi-step reaction with 6 steps

1: thionyl chloride / CH₂Cl₂ / 0.5 h / ice cooling

2: CH₂Cl₂ / 1 h / Heating

3: DCC / tetrahydrofuran / 4 h / 0 °C

4: tetrahydrofuran / 4 h / 0 °C

5: Et₃N / CH₂Cl₂

6: 95 percent / Et₂AlCl / CH₂Cl₂ / 10 h / -40 °C

With thionyl chloride; diethylaluminium chloride; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 6: asymmetric Diels-Alder cyclization;

DOI:10.1002/poc.828

Reference yield:

(S)-α,α-diphenyl-(indolin-2-yl)methanol (141410-04-0) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-2-(hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-methanone (234079-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

2: 95 percent / Et₂AlCl / CH₂Cl₂ / 10 h / -40 °C

With diethylaluminium chloride; triethylamine; In dichloromethane; 2: asymmetric Diels-Alder cyclization;

DOI:10.1002/poc.828

upstream raw materials:

cyclopenta-1,3-diene

1-[(S)-2-(Hydroxy-diphenyl-methyl)-2,3-dihydro-indol-1-yl]-propenone

(S)-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid methyl ester