(4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone
• CAS No.: 1393737-55-7
• Molecular Formula: C₁₉H₂₁NO₃
• Molecular Weight: 311.381
• Mol file: 1393737-55-7.mol

Synonyms:(4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone

Chemical Property of (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone

There total 7 articles about (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone 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: 47.0%

(S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol (1393737-36-4) + 2-Chloroethyl chloroformate (627-11-2) → (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-40-0) + (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-55-7)

Guidance literature:

(S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol; 2-Chloroethyl chloroformate; With pyridine; In dichloromethane; at 20 ℃; for 15h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 2 ℃; for 6h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tet.2012.06.090

Reference yield: 41.0%

di(succinimido) carbonate (74124-79-1) + (S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol (1393737-36-4) → (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-40-0) + (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-55-7)

Guidance literature:

In acetonitrile; at 20 ℃; for 15h; optical yield given as %de;

DOI:10.1016/j.tet.2012.06.090

Reference yield:

diethyl (S)-(α-methylbenzyl)aminomalonate → (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-40-0) + (4S,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (1393737-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: 18 h / 20 °C / Cooling with ice

2.1: lithium aluminium tetrahydride / diethyl ether / 2.5 h / Cooling with ice

2.2: 2 h / 20 °C

3.1: acetonitrile / 15 h / 20 °C

With lithium aluminium tetrahydride; potassium tert-butylate; In diethyl ether; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2012.06.090

upstream raw materials:

diethyl 2-benzyl-2-(N-((S)-α-methylbenzyl)amino)malonate

di(succinimido) carbonate

(S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol

2-Chloroethyl chloroformate