(S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one
• CAS No.: 1239015-87-2
• Molecular Formula: C₂₀H₁₈N₂O₃
• Molecular Weight: 334.375
• Mol file: 1239015-87-2.mol

Synonyms:(S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one

There total 1 articles about (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)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: 61.0%

quinoline (91-22-5) + (S)-4-benzyloxazolidin-2-one-3-carbonyl chloride (139149-49-8) → (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one (1239015-87-2)

Guidance literature:

quinoline; With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 ℃; Inert atmosphere;

(S)-4-benzyloxazolidin-2-one-3-carbonyl chloride; In hexane; dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0029-1219942

Reference yield:

(S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one (1239015-87-2) → methyl (3S)-3-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate (1239015-91-8) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: samarium(III) trifluoromethanesulfonate / 2 h / 80 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; samarium(III) trifluoromethanesulfonate; In dichloromethane;

DOI:10.1002/ejoc.201200344

Reference yield:

(S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one (1239015-87-2) → (S)-4-benzyl-3-[(1aS,7bR)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one (1239015-89-4) + (S)-4-benzyl-3-[(1aR,7bS)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one (1239015-88-3)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 18h; diastereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0029-1219942

upstream raw materials:

quinoline

(S)-4-benzyloxazolidin-2-one-3-carbonyl chloride

Downstream raw materials:

(S)-4-benzyl-3-[(1aS,7bR)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one

(S)-4-benzyl-3-[(1aR,7bS)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one

methyl (3S)-3-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

(S)-4-Benzyl-2-oxazolidinone