4,4-dimethyl-2-oxo-1-phenyl-3-pyrrolidinyl tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate

Base Information

• Chemical Name: 4,4-dimethyl-2-oxo-1-phenyl-3-pyrrolidinyl tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate
• CAS No.: 496785-31-0
• Molecular Formula: C₂₉H₂₇NO₃
• Molecular Weight: 437.538
• Mol file: 496785-31-0.mol

Synonyms:

Chemical Property of 4,4-dimethyl-2-oxo-1-phenyl-3-pyrrolidinyl tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4-dimethyl-2-oxo-1-phenyl-3-pyrrolidinyl tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate

There total 3 articles about 4,4-dimethyl-2-oxo-1-phenyl-3-pyrrolidinyl tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15-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: 87.0%

anthracene (120-12-7) + (S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl acrylate (252638-29-2) → (11R,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 9,10-dihydro-9,10-ethanoanthracene-11-carboxylate (252638-35-0,496785-31-0)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/S0957-4166(99)00267-0

Reference yield:

(S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (169221-12-9) → (11R,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 9,10-dihydro-9,10-ethanoanthracene-11-carboxylate (252638-35-0,496785-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / DCC; DMAP / CH₂Cl₂ / 96 h / 20 °C

2: 87 percent / TiCl₄ / CH₂Cl₂ / 18 h / 20 °C

With dmap; titanium tetrachloride; dicyclohexyl-carbodiimide; In dichloromethane; 1: Esterification / 2: Cycloaddition;

DOI:10.1016/S0957-4166(99)00267-0

Reference yield:

(R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one (169221-13-0) → (11R,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 9,10-dihydro-9,10-ethanoanthracene-11-carboxylate (252638-35-0,496785-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 0.17 h / -20 °C

2: 87 percent / TiCl₄ / CH₂Cl₂ / 18 h / 20 °C

With titanium tetrachloride; triethylamine; In dichloromethane; 1: Esterification / 2: Cycloaddition;

DOI:10.1016/S0957-4166(99)00267-0

upstream raw materials:

anthracene

(S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl acrylate

(S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone

(R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one