(4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 94418-35-6
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.408
• Mol file: 94418-35-6.mol

Synonyms:(4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 12 articles about (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-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: 70.0%

(4R,5S)-3-((E,E)-2',7',9'-decatrienoyl)-4-methyl-5-phenyl-2-oxazolidinone (94418-28-7) → (4R,5S)-3-((4'R,5'R,6'S)-bicyclo<4.3.0>nonene-4'-carbonyl)-4-methyl-5-phenyl-2-oxazolidinone (94418-35-6,94482-03-8) + (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one (94418-35-6)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; toluene; at -30 ℃; for 5h; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)90184-4

Reference yield: 70.0%

(4R,5S)-3-((E,E)-2',7',9'-decatrienoyl)-4-methyl-5-phenyl-2-oxazolidinone (94418-28-7) → (4R,5S)-3-((4'R,5'R,6'S)-bicyclo<4.3.0>nonene-4'-carbonyl)-4-methyl-5-phenyl-2-oxazolidinone (94418-35-6,94482-03-8) + (4R,5S)-3-((3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carbonyl)-4-methyl-5-phenyl-oxazolidin-2-one (94418-35-6)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; toluene; at -30 ℃; for 5h; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)90184-4

Reference yield:

(2E,7E)-deca-2,7,9-trienoic acid (90719-48-5) → (4R,5S)-3-((4'R,5'R,6'S)-bicyclo<4.3.0>nonene-4'-carbonyl)-4-methyl-5-phenyl-2-oxazolidinone (94418-35-6,94482-03-8)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride / toluene / 20 h / Ambient temperature

2: 65 percent / 1.) n-butyllithium / tetrahydrofuran / 1.) -78 deg C, 10 min; 2.) -78 deg C then r.t.

3: 70 percent / dimethylaluminum chloride / CH₂Cl₂; toluene / 5 h / -30 °C

With n-butyllithium; oxalyl dichloride; dimethylaluminum chloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00212a037

upstream raw materials:

(4R,5S)-3-((E,E)-2',7',9'-decatrienoyl)-4-methyl-5-phenyl-2-oxazolidinone

4-methyl-5-phenyloxazolidin-2-one

methyl (2E,7E)-2,7,9-decatrien-1-oate

(2E,7E)-deca-2,7,9-trienoic acid

Downstream raw materials:

phenylmethyl (4R,5R,6S)-bicyclo<4.3.0>nonene-4-carboxylate